EP. 186 — In Our Shameless Era with Simon Rex

Jameela Intro Hello and welcome to another episode of I Weigh with Jameela Jamil, a podcast against shame. I hope you’re well. Today’s episode is a bit of a different one. It’s more of a human interest story, and I don’t do those all the time. But I think that when the world feels particularly hopeless, I want something warm and hopeful and distracting to listen to. And I asked my lovely and fascinating friend Simon Rex, to come on to the podcast to tell us his life story, because I think it’s such a fascinating one. Now, of course, this is the tale of objectively a straight, handsome white man who has had a career in the most unrelatable industry on earth, the entertainment industry. But if you dig beneath the surface, his story is just bananas, uh, from childhood through to his unexpected entry into the industry and the spectacular highs and lows and then highs again of that journey, and what that does to someone’s psyche and the shame involved and the ego and the pride and the excitement and the gratitude and the humility, all of it. And he really lays his heart wide open in this chat. He’s such an interesting and unique human being, and it’s really hard to find men who are willing to really get into the nitty gritty of their journey, and who aren’t afraid of being honest about the highs and lows, and I love that about him. And I wish there were more people, especially men in the world, who were willing to do so, who were willing to unpack their journey for us. And so I love this story. I think he’s a really interesting and integral and decent human being. There’s a really great story towards the end about a time where at his lowest and his most completely broke and destitute, him being offered seventy grand to lie and say that he’d had sex with Meghan Markle when the tabloids were coming after her. And he talks about his decision making through that circumstance and what led him to what he ended up doing. And it’s just, uh, a really sweet tale of a good man who’s had a really unbelievable life. So sit back, relax and enjoy the absolute whirlwind that is the fantastically talented Simon Rex.

Jameela My good, dear friend Simon Rex. Welcome to I Weigh.

Simon Thank you for having me and providing tea. Very British of you.

Jameela Thank you for bringing me a green juice. Very LA of you.

Simon We’re even.

Jameela Yeah. Um, I wanted you to come here today because, cecause you’re my friend and I love you, but also because I think you have had such an interesting and unusual life story. And even though this industry can seem incredibly unrelatable, I think there’s a lot of really relatable things about your journey through this industry because it’s been such a wild ride and there have been so many high highs and low lows. And I’d love to talk to you about that and find out the impact it all had on your brain. So I guess I’ll just start by asking you, how is your mental health at the moment?

Simon Good question, uh, it’s always changing. I mean, it’s almost like when people say, “are you happy?”

Jameela Mhm.

Simon It’s like, well, sometimes, you know, it’s like a fleeting thing. And I think, uh, so much is dependent on my sleep, my diet, who I’m around, my environment. Uh, so my mental health changes all the time. Right now, I’m in a very good mood because I’m with a friend, and I had a healthy lunch, and, but, you know, this morning when I was in therapy, I was talking to my therapist, and I feel the need when I talk to him to always just say the bad stuff. And then at one point I said to him, but, you know, life’s pretty good. I just feel the need to vent to you about the list of notes I take that are the problems, but overall I’m really grateful, and life’s pretty good.

Jameela Mhm.

Simon And I, I just kind of, and again, this sounds very woo woo California, but I always just kind of come back to a place of gratitude because I just realize in looking around the world and seeing what’s going on in this business and in life, how fortunate I am to even just be working and have a home in the desert. And I almost feel, it’s hard to enjoy it sometimes because I feel almost bad about it. Because why, I have like imposter syndrome. Like, why do I get, why, why am I, why do I get it? You know, and I think I have low self-esteem, which stems from childhood abandonment issues from the family unit, which is sort of what I’ve learned over the years. It just makes sense that I, my parents got divorced when I was two, so I never had a father figure around. And what that does to you as a man, the lack of a male role model and father figure has a profound effect on your self-esteem, your relationships, all these things.

Jameela Well, listen, first of all, you shouldn’t have imposter syndrome because you are so brilliant. But imposter syndrome doesn’t really care about whether you’re good or not. But second of all you have had a fucking insane career and life.

Simon Yeah.

Jameela And I can imagine that part of the gratitude that you have now is because you know what it’s like to lose everything.

Simon Mhm.

Jameela And I would love to, you know, I think I feel quite a big affinity with you in that you and I both didn’t expect to get into this industry. We were both kind of plucked from obscurity and plopped in the middle of madness, and things just seemed to go incredibly well, uh, for both of us at the very beginning, in our 20s, and then in very different ways, things fell apart for both of us somewhere in the middle. And now we’re kind of scraping our way back up. And the second time around, you feel more ready for everything. You feel older, you feel wiser, your priorities completely change, and you are able to access a gratitude. And this can be in health. f you lose your health and then you somehow get some of it back. This can be in any area, but it’s really hard to really download gratitude into someone who doesn’t know what it’s like to lose it, but now you do. So can you talk to me a bit about how your career started and how it progressed? What happened? Because I think this is, this isn’t a story about actors or celebrities. This is a very human story.

Simon Yeah. I don’t think I ever was, uh, delusional enough to think that “I’m going to go make it in Hollywood or I’m going to,” you know, that was never the case. It really fell in my lap. And I think the what I will say that I did well was when I saw an opportunity, I went for it. And I come from a very average middle class Northern California background. I had, by the time I graduated high school, I probably had six jobs. I worked in a potato sack factory, I worked as a lawnmower. I worked at a gas station. I was a paper boy. I did telemarketing where you’d open a phone book and cold call and sell life insurance.

Jameela Oh, people love that.

Simon Oh, it’s a great job. And I remember going to community college and thinking, “oh, I’ll get it, I can’t.” Which I never understood how you’re supposed to pick your career at 18. I’m 49 now and I still don’t know what I want to do, but I have the body of a 48 year old. But I was at a rave in San Francisco in 1993, maybe 92, and this beautiful girl comes up to me and took my beanie off my head and ran her fingers through my hair. Long story short, she was a model, and I moved into LA and dropped everything and moved to LA with her and her two year old son. And I was in way over my head, and I was driving her around to her auditions, and I was working at a restaurant and her two year old son was calling me dad and I was like, okay, this is

Jameela And you’re what, 19?

Simon I was 19, 18, 19. And I was in way over my head, but I think I was just infatuated with beauty because I’d never been with a woman that was that beautiful. And she was a few years older than me. So we lived together, and I would drive around to her auditions or castings for modeling, and she had a scar on her face and she would never get jobs because this is before, like, you could, you know, computer remove. But she was really beautiful, and I remember her having a hard time because of the scar, which is what made her so unique and beautiful too. And one day I’m sitting with her son on my lap and the casting director comes out and says, “Who’s he?” And she goes, “Oh, that’s my boyfriend.” And I was right for the male part of this modeling job. Next thing you know, I go to Milan to do this job. We break up for many other reasons. And next thing you know, I’m signed with some modeling agency, and I’m living in Paris, New York, and Milan doing runway shows instead of going to college. And I was sort of thrown into living in Europe, which was amazing. And this is before the days of having smartphones. This is actually like before email. And I was, uh, I remember because I’d be writing letters to people from Milan, and I didn’t like modeling because it was very boring. And to go in and sit in another room with other dudes and be like, who’s going to be better looking and get this job was so lame to me. But I made decent money and I got to travel the world and I was like, this is awesome! But I knew it isn’t what I wanted to do. And then when I was a model, there was a male model named Marcus Schenkenberg. He was the first male supermodel. He was like the Cindy Crawford of the 90s, and him and Tyson Beckford and the whole Zoolander thing was based on these male models. And I was, uh, in the same agency, and there was, uh, he was, Marcus Schenkenberg was meant to be a guest on MTV. He couldn’t do the rehearsal. My agent, being smart, said, “Let’s send Simon. I bet you he’ll get a job out of this.” And I did, and I went to fill in for him. There was a VJ named Kennedy who interviewed, there was a show called Get Late with Kennedy on MTV, and I was rehearsing to see, what do you ask a male model? And I just was zinging and zanging with her. Producers loved me, and they offered me a job. And I’ll never forget, as a VJ and I said, “I have no journalism experience, I have no music experience, and I’ve never done anything on camera/TV like this.” And they said, “You’re perfect for the job, you got the job.” And I was, next thing you know, I’m live with a red light on in front of the world on MTV doing spring break, interviewing Madonna.

Jameela I remember.

Simon Interviewing Howard Stern, and that’s when MTV was the shit, like it was a very cool place. And, uh, living in New York in the 90s, it was awesome. I mean, just being in that world and being in MTV, you meet everybody athletes, rappers, actors, everybody came through MTV. So I met everyone and got comfortable to the point where after awhile I didn’t need to read the teleprompter, and I got comfortable enough with just improving and and then Gus Van Sant, famous movie director, auditioned me for Good Will Hunting. He saw me and he said, “Simon looks right for this part.” And I went into the audition, I’ll never forget this, and I sit across from Matt Damon, and I read the lines like a robot off of a page. I never acted, and in the middle of the audition, Gus Van Sant stops me and says, “Simon, I have to stop you. This is the worst audition I’ve ever seen.” And Matt Damon laughed at me and I go, “Yeah, I’ve never done this before.” And he goes, “You’re not ready for this, but you should go to acting school because you have something.” So I started taking acting classes in New York, like theater classes and Stanislavski and method classes and way out of my comfort zone again. But I was like, well, I should listen to Gus Van Sant. He knows what he’s talking about, you know, seen his movies and Drugstore Cowboys, one of my favorite movies of all time. And I started booking

Jameela But you also had like Calvin Klein campaigns and Tommy Hilfiger and all kinds of different things going on.

Simon Yeah, I did Tommy Hilfiger campaigns. I did, yeah, I did a bunch of modeling stuff. And that was sort of, it all kind of built up. And then I started, I moved to LA on a one way ticket after MTV released everybody. One day they fire all the VJs and hire new ones, and I remember they replaced me with Carson Daly. And I’ll never forget Carson Daly pitched TRL and it became TRL live, and he was smart. He came from radio, and he pitched TRL and he became the white guy who replaced the white guy. And I was very sad at the time, but looking back, it was a blessing because I got off of that VJ hosting island and into acting. This is back when they would give holding deals. So Warner Brothers Network, the WB, I remember giving me a holding deal saying, “We’re going to pay you this amount of money to not do other network shows.” And they started putting me on like Felicity and Jack and Jill, and I was the character who took Felicity’s virginity. It was J.J. Abrams’ first show, who I just saw at the Saturday Night Live party, hadn’t seen him since 1999 and went up to him, I’m like, “Hey, do you remember me?” He goes, “Of course I do. I’m so happy for you, da da da.” It’s J.J. Abrams, huge director, producer, whatever extraordinaire, and it was like his first big thing was Felicity. And I just was so, not cocky, I think I was just, uh, I don’t know what the word is

Jameela It’s too surreal. It’s not even cocky. It’s too surreal to understand what’s happening.

Simon Yeah, it happened to me.

Jameela There’s no way to prepare for it. If you’ve gone to drama school your whole life and you’ve been preparing for it, even then, you’re still not ready for it. Unless your parents are in this industry and you’ve grown up around it and you actually have a firm understanding. It’s so bonkers to go from a potato sack factory right into the epicenter of the wildest industry in the world. So you’re now booking everything, you land Scary Movie, the Scary Movie franchise.

Simon Right.

Jameela In which you were exceptional.

Simon Thank you.

Jameela And then what happened?

Simon I was doing a sitcom with Amanda Bynes that was called What I Like About You. And it was, there was a lot of money in Hollywood at the time, and between Scary Movie and the Warner Brothers Network, I bought a nice house in Laurel Canyon.

Jameela Mhm.

Simon And I bought a Porsche, and I was that guy driving around in my Porsche showing up at auditions, basically hung over, not knowing my lines, booking everything. Right?

Jameela Right.

Simon I have been very fortunate that these things fell into my lap. And then I was working, working, working, and I think, I didn’t take it for granted, but Adrien Brody was a very good friend of mine, right when he won the Oscar for The Pianist, me and him were best friends, and this was early 2000s, and he was making beats all the time on a little drum machine, and he taught me how to make beats on this little Yamaha keyboard. So as a hobby, he goes, “Look, if you want to be an actor, there’s a lot of downtime. You need another creative outlet.” So I really got into producing music as a hobby, and I was introduced to these two rappers named Mickey Avalon and Andre Legacy through a friend of mine who was in and out of prison who was like, “You got to meet these rappers I grew up with.” I’m like, “I don’t want to meet any rappers. I’m acting. I got a career. This is just a hobby.” He goes, “Trust me, meet these guys.” Cut to Mickey Avalon’s living on my couch. Cut to were burning CDs that we made in my spare bedroom. I’m handing them out at nightclubs to like, Leonardo DiCaprio and handing them out to people like, “Hey, check out this fun thing I’m doing for fun. That’s a joke.” Next thing you know, Interscope Records signs Mickey Avalon. Next thing you know, we’re opening up for the Chili Peppers in Europe in front of 60,000 people. Next thing you know, my agents calling me going, “Simon, we have a big audition for you blah blah blah.” I’m like “I’m in Poland with the Chili Peppers,” and they’re like, “What are you talking about? Why?” I’m like, “I don’t know what’s happening, but it’s fun and I’m doing it.” After a while, my agents stopped trying to get me jobs because I was on the road living this alter ego named Dirt Nasty, which was a rap persona that I created, which was a comedic character making fun, the joke in my mind was, you always hear rappers talking about selling drugs. I said, “I want to be the customer.” That was the joke. I’m the Hollywood scumbag customer who’s partying, and I created a monster that was a very heightened, exaggerated version of myself.

Jameela There are so many rumors about what happened to your career, right? Because we all were there watching you just go from strength to strength to strength in like, what feels like if someone made a movie of your career, people would say, “Well, that’s just not realistic.” Because it went so well. But then there are a bunch of different rumors as to what happened to your career that then led you to the existential crisis at 40 that you were in when we first met. Can you talk a bit about that?

Simon So the girl I told you about with the scar on her face, she was, uh, doing naked magazines, like, similar to, like, Penthouse or Hustler. And I was 18 years old, right out of the potato sack factory, and I thought it was the hottest thing in the world. I got this girl who’s comfortable with her sexuality, and I grew up as a hippie, and being naked wasn’t a big deal.

Jameela Mhm.

Simon And I remember her and I were dating, and we were raising her two year old son and the rent was due, and she goes, “Hey, I’m doing these, these photoshoots, will you do one too to help out and pay the rent?” Like, sure. No big deal. Well, cut to, years later those pictures surfaced of me naked, uh, when I worked at MTV. And I’ll never forget, because this is when the internet first came out, and I remember it kind of being leaked on the internet and MTV, uh, there was like a scandal around. And then MTV was sort of forced with, like, “Do we fire him?” And I’ll never forget they called me into a meeting and it was in office like this, and they said, “Okay, Simon, did you have sex on camera?” I go, “No.” They said, “Do you have sex with an animal on camera?” And I started laughing, I thought they were joking. They’re like, “No we’re serious. Is there any animals involved?” I go, “No.” And they go, “Okay, well, we can’t fire you because Jenny McCarthy is essentially our biggest star. And she was naked on the hood of a car in Playboy, and what you did is essentially not that different, so you don’t lose your job.

Jameela These were videos of you alone, right?

Simon Yes. Exactly.

Jameela Yeah. No animals.

Simon I’m an only child.

Jameela Yeah.

Simon And no animals. I’m the only one.

Jameela Sexy videos that by the way, now

Simon Yeah.

Jameela You’d make millions. You’d make millions, that come out now, no one would shame you. There’d be no article. There would be such a ginormous backlash if you, if people tried to bring you down or hurt your career.

Simon Right.

Jameela Uh, over videos of sexual self-expression.

Simon It’s, for me, it’s not a big deal, but I understand that America is a very sexually uptight place, and it’s very corporate in that other companies were a bit apprehensive about working with me because if those pictures surfaced, it would taint their brand. So I, I was surprised it actually, like I remember I booked a movie called like Cheaper by the Dozen. It was like a Steve Martin movie that I booked. It was like, uh something dozen and

Jameela It was Cheaper by the Dozen. It was a huge movie.

Simon Yeah, I was, I booked that and then I think, I believe Ashton Kutcher replaced me and got the role because after I booked it, they’re like, “We can’t use you.”

Jameela Fuck.

Simon And this is early 2000s, I want to say, so I had a few jobs like that, that was like, oh man, I blew it. But then in a weird way, it also like, the scandal and the controversy also helped me get a lot of, I guess, attention maybe in the wrong way. It helped me get other jobs in sort of like the cool alternative indie movies, and nobody had a problem with it except a couple people. So I stayed working, and the rumor was, is that MTV fired me because of it, and it’s it’s a false narrative. What happens with MTV is they fire everybody and start over. And I was part of the sweep, but for whatever reason, it was around that time, so people were like, “Oh, he got let go because those pictures that Page Six was talking about because of the timing just seemed like that’s why.”

Jameela And also, if people think that a giant establishment has distanced themselves from you, then they think, “Well, we should also distance ourselves from you.”

Simon And that’s what happened.

Jameela Yeah.

Simon And then I sort of just had to live with that, live with that sort of shame and guilt that even

Jameela Did you feel shame and guilt?

Simon Well I did only because of the way society makes you feel.

Jameela Did your family feel any kind of way about it?

Jameela Yeah, you know, my mom, I remember my mom being a little bummed out at first, but then after awhile realizing, like after, you know, of all the other things that, you know, like things people have done, and, you know, I only hurt myself. Like, it’s not like I hurt anybody or did anything to bad, you know. After a while, it just sort of was like, “Oh, who cares?” And I think more recently I think, um, nudity and, and all these things have been really destigmatized because I think we’re moving forward and kind of growing up. I think America’s a very adolescent culture. I’m part of a byproduct of that. I’m still very childlike in a lot of ways, and like just blaming that on America. But we are the young, cocky like country that isn’t, you know, you go to other parts of the world and you realize how much more refined other cultures are. In America, nd you see American tourists when you’re in Italy or France or somewhere and you’re like, “Oh my God, no wonder they think we’re, I get it.” Um, and I feel like there’s a lot of changes happening right now, that being one of them. Some good and some bad. And part of it is I think we are growing up and through Covid, all these things like what’s important, what’s not.

Jameela Our values are shifting.

Simon Yeah.

Jameela So as your career started to transition away from the trajectory that you were on, how did your mental health feel then? Like you’re going out a lot, you’re partying a lot. I think you were starting to slow down by the time I met you.

Simon Yeah.

Jameela What was happening? How were you feeling?

Simon I think I was, in LA, I think Jim Morrison said “It’s the loneliest city in the world.” And it really is a lonely place. It’s, uh, a very transactional relationship. Everybody here is in one business, show business. Everyone, no one says, “How are you?” They’re like, “What are you working on?” Because they want to know how they could benefit from you. And when you’re, when you’re hot, your phones ringing and when you’re cold, no one wants to get near you. And I experienced that. I remember being hot, the hot thing and then not having a lot of heat. And, you know, I think I’m very sensitive and I take things personally. And I was, you know, made the mistake of thinking that maybe I was lesser than because I wasn’t working and the phone wasn’t ringing as much, and you’re kind of left with, I’m sitting in this beautiful house in the hills that I had to sell because I couldn’t afford it anymore. And I just turned 40, and I kind of went through my woo woo spiritual phase of going to yoga every day and getting all the self help books.

Jameela I remember this. You were going to kundalini like every fucking day.

Simon I was going every day and it was working. And then one day I remember the teacher saying, “You know, people say we’re a cult. You know what? We are a cult.” And I remember looking around and everyone was wearing all white but me. And I go, “Oh, I better get out of here now before I wear all white.” It was like the moment of like, you know, and I remember having the wherewithal to be like, “Okay, I’m out of here.” And I could see how people get lost in that with community. And you sort of get high with these breathing techniques, and it’s sort of like, you know, I was, I was the perfect vulnerable person to be, uh, susceptible. Is that the right word?

Jameela Yeah.

Simon To being kind of pulled into a group of people in a group think. And I’ve always had an aversion to group thinks.

Jameela Yeah. Same

Simon I don’t like us and them thinking, binary thinking, but we all do it. I catch myself doing it all the time. Us and them thinking, and I think that I’ve always been, as an only child, kind of a lone wolf, but I think that’s a superpower. And I think a lot of people can’t sit alone with themself for five minutes. And I again, as an only child, I spent a lot of time alone and know how to entertain myself, so I was okay. I think my mental health at the time was, it was an exit. It was midlife crisis.

Jameela You were definitely manic.

Jameela I was, oh yeah, I was manic, I was, I remember quitting weed, which I’d smoked weed to kind of like looking back, I was just sort of checking out. You know, to me it was, “Oh, it’s just weed.” Because I was never much of a drinker, but the weed had become so strong. I remember weed became like legal and weed was becoming like this other thing where I was abusing it, and I was just sort of checking out and playing video games as an escape and just staying home. And I just didn’t feel happy. I was definitely just numbing myself, and I so I quit the weed and all of a sudden I’m having these crazy, it’s like, almost like you’re putting a lid on your emotional growth and you let it off. When you stop and all of these things start coming up that you’ve been suppressing, you know, emotions, dreams, all this shit. And I just was really sitting in it in the uncomfortable ickiness.

Jameela By yourself.

Simon Yeah, mostly.

Jameela In a house in the hills.

Simon And I’d have girlfriends, but when we met, I was single, and it was sort of something sad about being like 40 and single and no kids and no wife. I think I was just sort of, which is what society makes you feel like, and, and, and I get that, but I also see a lot of people rushing into marriage and, and kids maybe with the wrong person. And I was like, “I’m never going to do that.” And I was just at this crossroads and selling my house was like a humbling thing. So I downsized and I got a place at the beach in Santa Monica and Venice for a while.

Jameela Mhm.

Simon And I just said, “Well, you know what?” I just accepted it. I was like, “You know what? I had a good run, I think it’s over. The phone’s not ringing. I don’t have a legit agent anymore. I actually asked you. I was kind of joking, but not really. I’m like, “You should be my manager.” Because you believed in me so much when we talked. You’re like you, you just gave me confidence. And I remember like half jokingly saying, “You should be my manager because if you were on the phone, you’d sell me.” And I was just kind of, that’s where I was at, where I was asking someone who I knew for a few months, “You be my manager?”

Jameela Yeah, hahaha! I totally would have been your manager.

Simon Yeah, you would have been a great manager.

Jameela I knew you were special from the minute I met you.

Simon That’s very nice.

Jameela It was just like, you know, you’re like a bolt of lightning. And I remember thinking, like, I was like, “I’ve got write something for him.”

Simon Aw.

Jameela I’ve got to write something and put him in something because I just think, I think he’s so underestimated. And I think, you know, because this comedy sort of pervy rapper alter ego that you created.

Simon Yeah.

Jameela Although my dick is still a great song.

Simon Yeah. It’s a classic.

Jameela I stand by that song. I will walk down the aisle to that song one day. Um, but I, but I, hahaha, but, um, you know, it was, it was definitely far removed from the as I said earlier, the trajectory that you were on and like, I remember you having, like, a sense of quiet, low self-esteem or not belonging amongst people who used to be your peers.

Simon Yeah.

Jameela You now felt embarrassed around those people?

Simon I still do. I still don’t feel like I fit in. Like when I’m with a bunch of actors, I’m not like “I’m one of them.” When I was around musicians, “I’m not one of them.” When I was around models, I’m like, “I’m not one of them.” I never felt like I was a part of anything.

Jameela It’s because you and I belong in clown school.

Simon Yeah, I would love to go to clown school actually. I still want to do that.

Jameela Those our are people. We’ll do that together.

Simon I would love that.

Jameela So when you left and you left L.A., and then you went to Joshua Tree and just kind of went, “Okay, I’ve had a good run. I’m done.”

Simon Truly surrendered.

Jameela Yeah. You fully surrendered.

Simon Truly, yeah.

Jameela You fucked off to the middle of nowhere. How the fuck did you get here? Where you’re now like, winning massive, like beating A-list iconic actors to very big acting awards, uh, where you’ve had the biggest year of your entire career, I would say. What happened?

Simon I was literally laying on my couch in Joshua Tree looking at the ceiling fan, sort of at peace with the fact that I was only done because the industry was done with me. Because you can’t control, there’s only so much you can control, you know. And I was laying there and just in this point of just like, “Okay, here, I’m in the desert, let’s see what this brings. Like, I don’t know what’s next, but I’ll deal with it.” And then I get a DM on my Instagram from Sean Baker, who directed Red Rocket, the movie your speaking of that changed everything.

Jameela He’d done Florida Project and Tangerine. He’s like a, he’s an extraordinary genius.

Simon He’s brilliant, brilliant guy. And it actually wasn’t a DM. He had DM me and I missed it. And a mutual friend of his sister and mine’s, my uh, it was like, “Hey, can I give Sean Baker your number? And I was like, “Of course.” And he calls me up and he’s like, “Hey, man, um, I know you don’t know me, but can you put yourself on tape right now on your phone and send it to me for, uh, this, this movie? I’m just sending you one, like a two paragraphs. I just want to see if you’re right for this.” And at the time, I had, my hair was rainbow tie dye because it was the middle of the pandemic, and I was like, it’s all over. I’m gonna dye my hair rainbow. It was like cheetah print.

Jameela God, that really is the epitome of midlife crisis.

Simon Oh, yeah, yeah.

Jameela Cheetah rainbow.

Simon Oh, yeah. Cheetah rainbow. It was just like I could do whatever I want, I don’t care, I don’t need to be ready for an audition. And I was just like, and in a weird way, I kind of was like, in a weird way, looking back, I was kind of enjoying the fact that I could just now just not be like duh duh duh, accept me, hire me, I’m good enough. You know, it was over and I was okay with that. I was kind of like relieved. And then, no, it wasn’t over. And I guess the little audition I sent in, he loved it. And next thing you know, he’s like, “I need you to be in Texas in three days, but we can’t fly you here because we’ll have to quarantine you for a week, and the movie’s going immediately.” And I drove with my girlfriend at the time, three days to Texas as a memorizing. I’m on every page of this. It was the most I’ve ever taken on. And I’m, like, memorizing the script. And I get there and I’m prepared. And it was just one of those once in a lifetime magical opportunities where I don’t even think I knew at the time. It all happened so fast. It wasn’t like, “Oh, I got to kill it because this is it.” It all just happened and there was a flow and me and Sean just had chemistry, and the movie came out very special, and I and I found my guy who was like, what you want? Like, someone needs to give this guy a shot. And then later he said, I always wondered why this town didn’t give Simon a shot. I always believed in him. I always saw his Vine and Instagram and him in little movies here and there, like, why isn’t he working more? And he gave me a shot and it was just one of those like as soon as I, you know, surrender, I got pulled back in and I’m like, “Okay, here we go.” And since then I’ve been doing, I’m not allowed to talk about a lot of them because of the strike, but I’ve been working with like Oscar winning actors and the best directors and doing, you know, HBO pilots and NBC shows and all the things that, you know, went away, I got back now. And I’m totally now humble, head down, work hard, just want to work. And it’s so simple now because I’m not distracted with all the other things. I’m just ready for it all.

Jameela So one of the things I want to talk about is the fact that, interestingly, this is just the strange way that the universe works: the part. Can you describe the part that you played in Red Rocket?

Simon I play what’s called a suitcase pimp, which is basically a low level pimp who pimps girls in the adult film industry and also on camera having sex with the girls, but mostly though he’s a pimp. And that’s how Sean described it uh, because at the very end of the movie, that’s the line that sort of really agitates me. If you’ve seen the movie, that’s the line that they call me, and it’s like an insult. But I basically play a hustler, you know, like a very broke, narcissistic hustler. And I think, “Okay, I can tap into this very easily.” I’ve been I’ve been around enough of these people. Like, unless I’m lying to myself, like, I don’t think I’m a narcissist. I think I have been around so many, this culture is very narcissistic. America’s s this way. Everything’s going on. I was able to tap into that guy very easily. I think maybe, I don’t know if you can phase out of being a narcissist. I ask my therapist all the time “Am I a narcissist?” And he says, “The fact that you’re asking me means you’re not because you’re self-aware enough to ask.” It’s the people that are like, “No, I’m not a narcisscist.” Those are the ones that usually are.

Jameela Mhm.

Simon I might be self-centered, I might be selfish, I might have some of those things. But I played the ultimate narcissistic, abusive, manipulative gaslighter ever. And to be honest, it was fun to play an unredeemable horrible person as, it was like a character study, you know, the movie.

Jameela It’s also like a purge of any shame anyone has ever put on you. You’re playing now the most depraved and deplorable person in society. And what’s interesting is that he doesn’t like finding obvious people. He likes finding people who’ve either never worked before or haven’t worked in a very long time, and they often shoot into, you know, stardom afterwards. But he probably wouldn’t have called you

Simon Correct.

Jameela If your life hadn’t taken the turn that it did.

Simon That’s that’s very correct because he, had I been working as an actor this whole time, it would have been an easy, cause there was a lot of big actors who wanted this part, and he’s like, “I don’t want a big A-list name for this. I want a surprise.” And that’s part of his genius, is that he wants to take a different back door, and he street casts. Most of the movie he found on the street in Texas. And I was, besides the woman Bree Elrod, who played my wife, who’d done a lot of Broadway plays, no one else had ever acted in anything before. He provided a world for me to play in that was so much fun that it didn’t even feel like work. He let me improv a lot, um, in the end, I think the movie was like 30% improv, and him trusting me and letting me do me is what works, you know.

Jameela When you were standing on stage and accepting a very prestigious award, it was the Independent Spirit Award.

Simon Yeah, the Independent Spirit Award.

Jameela Which is like the night before the Oscars or something ridiculous like that. It’s, um, everyone in the industry is there. It’s for real actors, real writers, real performers, like, who make really meaningful work. What did it feel like up there, given everything that happened leading up to this, including your childhood, which we’ll go into in a minute, but what did it, what could that possibly have felt like? Are like people coming out of the woodwork who hadn’t been around for a long time? The phone suddenly starting to ring, like what happened up there?

Simon It’s funny because I wrote with Jeff Ross, a comedian friend of mine. We wrote because he’s like, “I have a feeling you might win. Let’s write some jokes if you win.” So we wrote all these jokes that I like memorized, and then as soon as I got up there, it all went out the window. And I’m glad it did, because I just spoke from the heart. And I remember just being, uh, up there, like, kind of like I was just realizing, like, the cosmic joke of life was so funny to me that here I am accepting, like the best actor award. It’s kind of one of those things like, again, I never wanted to be an actor, but whenever you are in this business, you’d be lying if you didn’t say, God, I wonder what I’d say if I was ever up there, like, what’s that moment like?” And then the moment’s happening and you’re sort of in shock. It’s almost like being in a car accident or getting in a fight where time slows down and you’re, you are in, I was in shock. And I don’t remember, only because I’ve watched it back everyday at dinner, just kidding. I watched it back and I was like, “Whoa, it’s so weird psychologically to look at myself and what was happening.” And I just truly was just like, it was like catharsis or something. And I was just thanking, and the funny part was, I brought my mom as my date, and she was sitting right there, and I forgot to thank my mom, and she was right there. My mom let me be a silly goose my whole life, and never questioned when all these things in my life happened, and I should have thanked my mom. And I remember afterwards apologizing, she’s like, “I don’t care about the fucking thank you.” And I never forget after Dirt Nasty and all this stuff in my past to be able to send my mom home in an Uber and hand her like the Best Actor award and she’s like crying, holding the award as I sent her home to because she was tired and exhausted from the night. It was like, finally I made my mom proud, you know what I mean? It was like, uh, albeit that it’s a trophy, but it was like, you know, that for the first time in my life, people are looking at me differently. They’re looking at me like, not as Dirt Nasty, not as the MTV guy, not as Scary Movie, the guy who slips on the banana peel. I was actually, like, respected, and I wasn’t used to that. And it was sort of like, it’s strange and it’s still happening, and it’s just a very interesting thing and seeing how people treat me different. And there’s a lot of people who are gonna fake kissing my ass now, and I kind of know what’s happening, and it’s just, it’s just

Jameela How does that feel?

Simon It’s weird. It’s weird.

Jameela Yeah, I’ve gone through that.

Simon Yeah. You know what that’s like. People hitting you up that maybe you grew up with or people in the

Jameela All kinds of cousins.

Simon Oh, yeah. It kind of makes you isolate more in a weird way.

Jameela Yeah.

Simon It makes you retract. It’s not like you step into it and you’re like, “Yes.” It’s almost like the opposite.

Jameela Well, you know the machine now cause you’ve been in the middle of it. You’ve been chewed up, spat out and then brought back in. And I feel very similarly where I’m just like, “Okay, so not everyone is my friend, and”

Simon Right.

Jameela Just come in, keep your head down, find your friends, hopefully outside of this industry, mostly. Keep those people very close so that you don’t become a prick and just try to stay safe. Like someone said to my boyfriend once when he was being fucked around by a lot of people in this industry, he was like, “Oh, you’re in the snake pit. You can’t get mad at the snakes if they bite you.”

Simon That’s exactly right.

Jameela You’ve chosen to enter the snake pit, and I don’t think people realize how much of a snake pit this really is. It’s so funny how much people long to be in this industry. And it is an amazing, amazing industry. You get to amazing things, uh, we live in an extraordinary amount of privilege compared to any other industry in the world that I can think of, if you are lucky enough to be successful in this town. But it’s, you know, no one’s doing anything particularly noble like being a doctor or a nurse.

Simon That’s right.

Jameela We’re not saving any lives, but it’s so interesting how people long to to do this career, and they have an idea of what fame and attention and being in the in crowd and, you know, all the cool people, whoever gets picked as the new cool crew, being able to hang out with those people, it’s so interesting how intoxicating that looks from the outside, but actually it becomes quite toxic when you’re in the middle of it. But you really were like right in the middle of it, right in the 90s when it was really exploding. And you talk about the fact that you didn’t think that was actually very good for you, and it wasn’t a very happy experience, like the fame of. It doesn’t make you happy.

Simon What’s the joke we we’re talking about from, uh, Extras? Fame is a mask that eats away at the skull, but it’s really the soul, but that was a joke in Extras. And it’s true, and fame is what everybody wants, and it’s actually the worst byproduct of what happens because you never really know who’s really your friend or if I meet a woman, I don’t know, does she really like me, or does she think that I can help her career if she’s in the business? Or, you always have to sort of be aware of that.

Jameela I remember something crazy that happened, um, but you were dating someone who for a while when I knew you years ago, who you thought just didn’t know who you were and didn’t know anything about you, and then you found out six months in or something to dating them that, you know, after so long of her pretending to just be like, “Oh, yeah. Oh, you’re an actor. That’s so interesting.” You found out from a friend of hers that she’d grown up with a picture of you on her wall.

Simon Yeah.

Jameela She was like a superfan.

Simon I was just telling this story earlier to my therapist.

Jameela I was telling this story to James, like, earlier today, where I was like, that was one of the fucking maddest things I’d ever heard, like I couldn’t imagine having to handle that.

Simon Yeah. That’s weird, that, and yeah you just feel kind of dumb. Like, how did I not see this in you? So, you know, because how do you know, you know? And so you always have to be aware of that. It’s sort of it’s not just with women, it’s actually interesting how men as well want to sort of attach themselves to you because you can help them. And it’s a really, LA there’s a very desperate energy here in the air, and it’s a very sad sort of dire, uh, place because the vibe here is like, everybody just wants that thing and they think you can help them get it, and it doesn’t really work that way. And I can never imagine doing that to anybody else. I’m surprised how often it happens to me.

Jameela Even now?

Simon Yeah, it’s still, sure, like

Jameela Do you think you can see it more clearly because you’re older?

Simon I think so, because I don’t think you’re smarter. I think you’re just wiser and you just have more life experience and life, I’ve just been around the sun more times, you know. And I think it’s just life experience, and you can’t learn that until you go through it, that’s not a book smart, that’s life smart, and that’s just

Jameela We’ll also you’ve buried a lot of your demons, like a lot of your codependency’s going away. You were lonely and codependent. And I think I was the same. I think we became codependent with each other when we first became friends. I think we hung out like every day for a period of time.

Simon Yeah, we did, we did, we did.

Jameela So some of the work that you have done to get wiser, aside from just getting older, is that you have been working on all the childhood trauma and childhood stuff that would have probably made you more blind to, you know, all of these things and unhealthy lifestyles, etc.. Like all that stuff when we were in our 20s, we’re not aware of it. It kind of starts to catch up with us in our 30s and then really, like comes after us if we haven’t, if we haven’t dealt with it in our 30s, it knocks the fucking door down in our 40s and then we dye our hair cheetah rainbow.

Simon Mhm. That’s right.

Jameela So can you talk to me a little bit about how your youth shaped some of the patterns that you then had to work through as an older person?

Simon Yeah, I think, uh, so my parents were divorced when I was two, and, uh, my father moved away to Hawaii, so I was kind of just alone with my mom. And my mom told me that I was acting out a lot when I was like, 3, 4. I feel so bad for my mom. I must have put her through hell. I was like a problem child, you know? And I was in therapy at a very young age, and looking back, you know

Jameela Why were you in therapy from such a young age?

Simon I was, I was acting out in school. I was, my mom said I peed in the refrigerator. She came home and I was a little kid, and I opened the refrigerator, and I’m peeing in the refrigerator. And she’s like, “This is all you acting out because you had no dad around, and you were just, you know, uh, uh, feral.” Is that the word?

Jameela Yeah. Feral’s a word

Simon And she would be like, she was a teacher and she’d stay late and I’d be by myself. It was just like I was kind of left to my own devices. And I think those formative years without a father figure around who gives you a deep sense of, uh, of low self-esteem, right? I think it kind of molds you in a way where you’re like, “Well, if my dad’s not around, then I’m not lovable.” So it took me a lot of work to realize I am and that it’s through therapy. EMDR, which you turned me on to when we first met, which I tried, which was very helpful, um, eye motion desensitization reprocessing, I believe, is what it stands for. I’m always trying different types of therapy. I did like mushroom therapy, and then I ended up actually one day having a psychedelic experience and came out of it saying, “I need to forgive my father, for him and for me.” So I called my dad.

Jameela Had you had a relationship this whole time like since two?

Simon Yeah, I’d see him once a year for a couple weeks, but, you know, it wasn’t really, we didn’t have a lot of time spent together, you know. There was not a lot of time, like, if you were to add up the accumulative days between when I was born to when I moved out of the house at 17, it wasn’t a lot of time spent. And then my mom remarried a guy who was an alcoholic and a cocaine addict, and I remember coming out to watch cartoons on a Saturday morning, the TV was gone because he’d swap it for coke, and I didn’t understand why the TV was gone. Or I’d get like five bucks a week allowance, and I’d save it for a couple of months and my allowance would be missing. He’d take it for Coke, and I’d be going to Al-Anon meetings in San Francisco and Oakland as a ten year old kid, because my stepdad was an addict, so it really ingrained in me at a very young age how evil alcohol and cocaine are, which is why I think I steered towards like marijuana and psychedelics. To me, in my mind, those were not as evil, albeit it was still an escape, but it was to me coke and alcohol are the devil. And I just saw what it does, and I grew up in a household with a lot of yelling, and I thought that’s how you communicated. And I saw that playing out in my relationships later, that I was just duplicating that, and that’s not right. So, I said to my dad, I called him up, I said, “I need to talk to you.” And I sat down next room and I said, “I forgive you.” And I watched physically the weight come off his shoulders and he cried. And ever since then, we’ve kind of had this shift in our relationship. And my dad, uh, is like an old hippie who lives in North Carolina now. And now we text more than ever. We talk more than ever. We’ve become, he said to me at one point, he goes, “You know, my dad pulled me aside at one point and he said, I’m not your father anymore. I’m your friend now. And he shook my hand.” And my dad did that to me. He said, “I’m not your father anymore. I’m your friend now.” And I still sit with this, and I think that’s either the coolest thing ever or I don’t or not, I don’t know. But what happened was this, that this father son dynamic kind of became like, we’re two adult men and we’re on the same level. And I knew what he meant, and it just kind of changed everything for the better. Yeah, I don’t think I’ve completely forgiven. I don’t think I’m completely over it, but enough to where, it’s almost like I take strattera for my ADHD and I’m 30% better because of it. And I feel like even that’s enough sometimes, and I feel like me saying I forgive you and working through most things have made our relationship significantly better, say more than 30%.

Jameela And what’s the, what’s the point of reconnecting with a parent?

Simon I realized how fast

Jameela Do you feel like you get anything from them beyond the kind of and I say this like, I know I sound like really cold and arbitrary, but I don’t, I don’t talk to a lot of my family. And I don’t really see the, uh, point in talking to a lot of the people that I just happen to know on a kind of technicality of DNA, um, if there isn’t actually something really there for, that would heal me or, um, teach me something. I don’t mean to be rude about that, but, you know, like, there are certain members that I do talk to, some that I don’t. And I have kind of grown a family out of friends, and they’re all people who are in my life on the merit of how we hold each other and what we like teach each other and the support and the love and all of these different things. So I wonder what it is that people are looking for when they reconnect with a parent. Is it just to know, oh, I wasn’t rejected like this was just an adult, this is just, this is someone who was young and wasn’t ready to be a dad?

Simon Yeah.

Jameela And it wasn’t personal. It wasn’t about me.

Simon Yes.

Jameela He does actually like me. He does love me. This isn’t like a fundamental thing that I am missing. This wasn’t about me.

Simon That’s exactly right. That’s exactly it. And it’s really that simple, but it’s it’s almost like, you know, when you’re going through a breakup and everyone’s like, “Oh, you know, it sucks now, but you’ll get over it.” You’re like “Yeah, but it sucks now.” That’s kind of how it was for a very long time, and I feel like I wanted to not live with that, uh, feeling anymore. And I wanted him to not live with that feeling anymore. And I knew that I was realizing how fast the trajectory of life was moving. And I’m getting older. I’m like, “Oh, how many more Christmases do I have with my folks? How many?” I started doing the math and I was like, “I don’t want it to be too late, and me, if I’m having these thoughts and I want to say these things, I’m not going to not say them.” I just wanted to let it be known. You know, my dad is a breathwork coach.

Jameela Mhm.

Simon So he, uh, I grew up around very, you know, hippie kind of world. You can have these conversations. It’s not like I grew up with this, you know, stern dad who was, you know, I never actually had that. I had the lack of discipline. I had the lack of father figure that I was kind of left to my own devices.

Jameela Who then got replaced with a junkie.

Simon Yeah, yeah.

Jameela What was that guy’s vibe like? What was his mood like?

Simon Well, thinking back, I was probably like, I want to say I was maybe 8 to 15 in that window of time. And looking back, I didn’t know at the time, it was very erratic and hot tempered and it was cocaine, you know, and and I didn’t know at the time. You don’t understand that when you’re a kid, but now looking back, I’m like, “Oh, that explains why he was doing these certain things all the time.” Everything starts to kind of fall into place. And I’m so glad that my mom now has met a man who she’s married to who is the sweetest man in the world is like, for instance, I’m going to meet him this weekend. He’s teaching me to build this outdoor kitchen at my house, and he’s, uh, real, uh, man’s man, um, but not in the cheesy, macho way, like, he’s actually a quiet saint. He’s like six foot seven. He could build anything. He’s quiet.

Jameela What’s that line that Anne Heche said to Harrison Ford. She said, “He’s just one of those guy guys. You can send him into the forest with a pocket knife or s Q-Tip, and he’ll build you a shopping mall.”

Simon That’s it.

Jameela Yeah.

Simon That’s this guy. And I’m just happy my mom’s got a great guy now. Now when I spend time with my mom, I get to have a cool guy around who’s, you know, teaching me all the things that I never really had as a kid that were like, you know, just things like that. Like, I know it might sound kind of corny, but those are the things I think that a guy needs is something like, you know, how to build something. I know it sounds silly, but it’s so simple. And I think it’s quite

Jameela It’s symbolic of something.

Simon It is.

Jameela You know, because you’re also, you need someone’s going to teach you how to build your life, how to build your brain, how to build your own world. And you didn’t have that. You just had a lot of dysfunction, a lot of abandonment.

Simon That’s correct. Also in our work, I imagine, like I’m always, this is sort of our life. It’s like you go do a movie for six weeks, and then you form these deep bonds and then it’s like, “Bye.” And it’s just over, so it’s so extreme. You go from like summer camp, bonding deep, working with someone and then you’re like, “I might not see them again.”

Jameela But we’re good at that because we’re used to losing people.

Simon Yeah exactly. And there’s something kind of sad about that. But also I, I think I have a novelty seeking brain and I get bored with routine.

Jameela Well it’s cause you have a dopamine deficiency.

Simon That’s exactly right.

Jameela Which is what causes the ADHD. It’s also really fucking hard to be young or older and not know you have ADHD and not understand.

Simon I didn’t know.

Jameela Yeah, and it’s amazing to know you now vs. Nine years ago.

Simon Wow.

Jameela Where trying to have a conversation with you was the most entertaining thing ever, but we couldn’t stay on one topic for more than a few seconds. It was like a ping pong ball flying around the room.

Simon You see, I’m actually listening now, retaining.

Jameela Oh, you’re a completely different person now to who you were 9 years ago.

Simon Because it’s ever since I won that award.

Jameela Yeah. Hahaha! And that is the point of this podcast everyone, is that win win an award and then your life gets sorted out, yeah.

Simon I do feel more relaxed in my, I feel like I’ve finally

Jameela I don’t think it’s just medicine. It just feels like you’re actually done the work and got the fuck out of this

Simon I think so.

Jameela Of the cesspit. So you just dip in and out and, and you make very different choices now to the ones you used to make. Like before, it wasn’t very, there was something kind of funny about you and me both being like, “Yeah, fuck it, whatever.” I’ve done so many stupid jobs, so many ridiculous things, and I’ve never really, I’ve sort of notoriously not given a shit about what I do because I’m just like, “Yeah.” Say yes, and show up. But then after a while you can end up painting yourself into a clown box and you have to become more intentional.

Simon Yes.

Jameela And it feels like you have learned a lot of lessons from the first time around where you’re just like, “Fuck it!”

Simon Yeah.

Jameela And now you’re actually taking it seriously cause you got such an amazing second chance.

Simon I did, and I say no to a lot of things now, and I, I’m very, very calculative. I’m not very much a planner. I never set goals. I was never goal oriented, like in three years I’ll be here or you know, I was never very good like that.

Jameela And the house and porche version of you has gone away, like the fact that you’re still building your own kind of outdoor kitchen or whatever.

Simon I’m so excited about that. It’s been the highlight of my life right now

Jameela Yeah, and it’s also because you’re, you’re not going after big sort of money jobs. You’re going after art.

Simon I’ve actually, I just remembered the day after I won the Spirit Award, my agent calls me up. He’s like, “Are you ready for this? We have seven offers on the table totaling X amount of money.” And it was like more money than I’d ever, and and we said no to all of them because they weren’t the right thing and then found something that was the right thing that felt right. And it was no money, but I knew that was the right thing to do. So I definitely am playing the long game, which is not like me. Before I would just impulsively, but I’m actually like, there’s a plan and a design to do really cool, special work with good people. And so far we’ve been executing. When I say “we” like my manager, my agent, we, I remember signing with my management saying like, “I know you guys don’t want to hear this, but I don’t want to just grab money and do all these big, I want to be very selective about the things I do because I’m in this rare moment where I can and

Jameela And after a lifetime of not being taken seriously, this thing that you didn’t even know you wanted, you didn’t even know if you were allowed to ask for it. The person I knew, I can’t imagine you ever daring to ask for that.

Simon Never.

Jameela But I think deep down, there was a dignity to you that you just kept on hiding underneath songs about your dick.

Simon That’s right. That’s exactly right. And like, I just did a movie. I can’t talk about it because of the strike. But I just did a movie and I said, “I want to be a producer on it. I want to be executive producer. I want to be creative. I want to, uh, pitch ideas. I want to be involved in the edit. I want to be involved in my wardrobe decisions. I want to do rewrites. I want to help cast it.” And they go, “Okay.” I go, “that’s all I had to do is ask?” So now I have my first movie that I’m executive producer of. I’m like, I’m leveling up to the point where I guess that’s, I don’t know if that’s confidence. I don’t know if that’s

Jameela Yeah, it’s confidence, it’s confidence. It’s no longer hiding behind, “I’m not worth anything. So I’m not going to put myself up to be taken seriously because I can’t actually back it up.” You finally come to a point in your life where you’ve done so much work and you’ve proven yourself.

Simon Yeah.

Jameela And maybe this healing with your dad that created the gaping wound of “I’m not worth shit, so why do I have to so I can do any old, like, embarrassing shit” Or whatever, and to not say that it was embarrassing, but I could do anything and not put any thought into it, because who gives a fuck because no one really loves me anyway.

Simon That’s right.

Jameela That’s gone. Or going.

Simon It’s interesting too because I’m, uh, part of me, it’s funny, I think it was what’s the director’s name? I can’t remember his name right now, but he said, “I don’t take myself seriously, but I take my work very seriously.” And that’s how I feel because I want to keep a little bit of that.

Jameela Don’t become a twat. I’ll destroy you.

Simon You know what I mean? Like I still, I love to laugh at myself and be the butt of a joke. And I think that’s the key to life is if you can’t laugh at yourself, you miss the punchline. And so many people take themselves way too seriously.

Jameela No, you gotta be Tom Hanks.

Simon That’s why we bonded. We both have a similar thing of like, we’re kind of a silly goose and it’s like, yeah, uh, I find that to be the secret to life. If you can laugh at yourself, you don’t miss the joke. And that’s a superpower. It’s kind of nice to just know that no matter what, like even if it was to end tomorrow because I already went through this, it’s going to be okay. I’m not dependent on anything or anyone. And that’s a very good place to be that you can’t be that in your 20s. You can’t be, you know, there’s a book actually about this called The Second Mountain that’s a bestselling book about in life, after you kind of go through everything and you do the things that you’re told to do and duh duh duh, and then you kind of go through this midlife existential crisis and then what’s that next mountain? And that’s sort of what I’m on and I believe you are as well.

Jameela Mhm.

Simon It’s, uh, that’s the good stuff. That’s the, that’s the jeuje. Um, I just am very, I feel like I’m self-aware, maybe I wasn’t before. I don’t know.

Jameela And you’re afraid of losing it this time. You’re more conscious of not throwing it away.

Simon Yes, and I’m normally not conscientious, um conscientious. I normally am someone who sort of walked through life kind of like not realizing that, like you’re saying, like having a conversation. I was just plowing over people and talking over people and not really listening, and like, I was just my blind spot. And I think I’ve just become self-aware of those things. And I look back at things, I’m like, “Oh my God, I was, I’m the constant.” Maybe in relationships with women, or maybe things, like I’m

Jameela Common denominator.

Simon Yes, but that’s so profound. And I remember learning when I was diagnosed and I had people take the term ADHD and use it very loosely, as if it’s just something that kind of is a fleeting thing that happens. But I’m technically have combination ADHD, which means that I have the hyperactivity and the attention span problem, as well as extremely sensitive. I feel everything to a fault. Well, I don’t know want to say fault’s the right word, but I feel things so much. I take things very personal and that’s all, you know, it’s not all of it, but that’s a part of it is. And learning that I had ADHD recently and getting on the right medication and telling my mom and dad, “Hey, you know it’s 75% genetic. One of you guys might have it, and they both took a test and my dad didn’t answer any of the questions. My mom’s like, “Oh my God, every single one.” I’ve been taking the wrong medication. The reason I have anxiety is because the root cause of buh buh buh. So now me and my mom are sharing, like, you know, we got a book on ADHD and we’re learning about it. She’s in her 70s, I’m almost 50. So there’s a lot of comfort in learning, like, “Oh, this is the reason why.” So there’s a lot of solace.

Jameela This is why you pissed in the fridge.

Simon That’s why I pissed in the fridge.

Jameela So tell me about the project that you are allowed to talk about because it is SAG permitted.

Simon That’s right.

Jameela And you’ve just been promoting it and

Simon Yeah, so.

Jameela I’d like to hear about it.

Simon Yeah, it’s a really cool movie when I was in Cannes for, and it is pronounced Cannes.

Jameela Yeah.

Simon I always was like “Con.” No, it’s Cannes and I’d always joke before I’d always be like, “You have any movies coming out?” I’d go, “Yeah, have one in Cannes, garbage can.” But now I actually movies in Cannes, and this one was in Cannes. It’s called Sweet East, and I was at in Cannes for Red Rocket, and the producer of the movie said, “Hey, I want you to meet this guy. He’s a DP. He shot Good Time. He’s sort of the go to guy who shoots all the cool movies in France, in America, and he’d like to meet you. And I meet him and he puts me in his movie, and it’s shot on film and it’s called The Sweet Eat, and it’s with Talia Ryder and Jeremy O. Harris and a great cast. And I basically play a white supremacist, and as someone who’s half Jewish, that’s pretty intense. I play a professor who’s very verbose and I, very much an intellectual, but he’s a he’s a racist, and he goes to white supremacy rallies and, um, and the movie just came out in Cannes and New York Film Festival. It comes out December 1st at the Angelika, and it’ll be in limited theaters, and then eventually it will be available elsewhere, but I’m technically the male lead in it, and, um, it was, it’s just cool to keep my feet in that indie arthouse world because it’s still funny to me that I’m even in that world with these, like, you know, true artists in New York, in Europe making these movies and in Cannes, they know, it’s just to me, it’s still quite funny. I don’t want to just start going and doing

Jameela You want to make the kind of films that inspired you when you were younger.

Simon I want to do shit that I would say, “Hey, go see this movie.” I would see this movie. How rare is that? Normally you’re lucky to get a job. You’re lucky to get a job that you’d be like, “Please don’t go see this.” You’re lucky to get that job. I’m in this point in my life where I’m doing movies that I’m proud of. It’s so rare. It’s just surreal. It’s such a, you know, it doesn’t, it doesn’t necessarily make you happy, you know, but it makes you feel like you have purpose. And I think purpose is a big deal, and people try to find purpose, and I think it’s, I found mine. I know this is what I’m supposed to do. I truly am here to entertain the.

Jameela So what do you, I don’t think you talk about your story with the hopes necessarily of inspiring anyone, but what do you hope anyone who listens to this story as, like, out of touch from reality as it can be because of some of the things that we’re talking about, but there are elements of it I think anyone can apply to their life. What do you hope people can learn from you talking about your story?

Simon Gosh, you know, that’s always a tricky one. I don’t know if I’m ever one to give advice, and if I’m being completely honest, I would tell people run the other way from show business because it’s a numbers game and it’s a lottery, and it’s it’s some of it is based on talent. A lot of it’s based on who you know and timing. And I’d give 25 years of my life to this. I sacrificed a lot. I don’t have a wife or kids, and I don’t know if necessary that’s a good or a bad thing. I don’t know, but I wouldn’t tell my worst enemy, “Hey, go to LA. You’re going to make it.” I think we we we lie to ourselves about a lot of things. And if you look at the numbers, it’s no different than saying, “You’re going to go to Vegas and hit the jackpot.” It’s kind of delusional.

Jameela Mhm.

Simon I would say in my situation, life just happened to me and I saw the opportunities when they came and I didn’t really operate out of a place of fear. I operated out of a place of curiosity and being open, and, um, I think that’s why I’m sitting here with you. But I still don’t know, I, I don’t know, and I don’t want to give you the cliche like, “Just be yourself,” but there is some truth to that. Um, I’m just being myself, and it’s working, and I feel like the people I see around me in this business that do well and in life are just kind of comfortable with themself and they know who they are, and I think that takes time. I would say go to therapy. I would say if you can, if you’re privileged enough and there’s ways you can do it now for not a lot of money, like don’t be embarrassed by wanting to get help. I think that now we’re normalizing people like you and people like Neal Brennan, and people like Pete Davidson are doing so much good work in discussing these things that have been taboo for so long that it’s okay to talk about. And we’re like, it’s all changing and it’s okay to have, I don’t even know what the word is, I don’t want to say problems, but like conditions and traumas and childhood issues you need to work out like don’t be afraid to step into the shadow and go into the cave.

Jameela And also, I would say from both of our eyes, but especially what’s going on with you now don’t give up completely. Like when everything goes to shit, the amount of times in my life I’ve just been like, “Well, that’s it, it’s over.” Including just like maybe February this year. I was like, “It’s over, it’s done.” 2020 I you know, got piled onto by the internet so badly I almost died. I was like, “It’s over.” Uh, five years before that, around the time that we became friends, I lost all my money. I got really, really fucked over while trying to start charity, and my money got stolen from me. Uh, the road to hell really is paved with good intentions. And like, years before that, everything was over for me. Years before that, I got fucking hit by a car, and I brought my back, and I thought I’d never walk again. Like, time and time again life has felt, I’ve gone in and out of extraordinary opportunities that have been handed to me that I don’t know how. And then unbelievable hardship where I either want to kill myself or I’m actively nearly dying. And I can’t tell you enough how how often I’ve wanted to give up. And I’m so glad that I didn’t. And I hope that maybe this episode, uh, if you’re still with us, uh, which I hope you are, will be your maybe a reminder that you might need right now just to hold on because you never know.

Simon You never know.

Jameela You never know what’s coming. And it doesn’t have to be a fucking acting career. It can be anything. It can be love. It can be family. It can be the job of your dreams, or the home of your dreams, or traveling or getting to have a second or third act that you never could have imagined, but you never know. And so many of these things do happen for a fucking reason.

Simon Mhm.

Jameela And the older I’m getting, the more woo woo in that way I am becoming where I’m just like, “I wouldn’t be who I am now had it not been for every fucking awful moment in my life.” It doesn’t mean I’m happy about it. I could stand to be at least 30% less wise.

Simon That’s right.

Jameela Uh, if I didn’t have to go through some of the shit that I went through, but don’t discount it. Don’t give up. And don’t limit yourself to the parameters that you’ve given yourself or that others have given you. Just know that we’re constantly growing and learning.

Simon Yeah.

Jameela You would never have been able to reach the depths that you were able to with the projects that you’re doing now

Simon That’s right.

Jameela Had do you not lived through everything you live through, had you not eaten a bakery of humble pie.

Simon That’s right.

Jameela For seven years before you, you know, got that opportunity.

Simon Yeah, and I think I think one more thing I’ll say too, is if you look at your life like it’s a movie, it’s not always going to be good. Like those low points are actually, like failure is a good thing.

Jameela Vital plot points.

Simon It is important to fail and get back up and dust yourself off and keep on going. And and I think failure is important to have that. And eating the humble pie like there’s a, I remember I had this guy who sort of a, he was like a my acupuncturist, but he was kind of like my Yoda guru guy. And he said to me, “When the pie hits you in the face, enjoy it. Taste the pie.” If you take the pie in the face, it’s okay. And take a little taste of it and smile and laugh. And I feel like that’s profound wisdom. And I had an experience real quick, this last one. I remember this lady road raging next to me, and she pulls up next to me and she’s pulling her hair and screaming at me. And I looked at her and I just laughed. And then she realized how insane she was being, and she started laughing and she drove off. I was like, that’s it. That’s the, that’s it right there. Like, if you could laugh at it, just have some fun with it and and just laugh a little. And I feel like that’s why I’m here. I want to make people laugh. And I know this is, what we were, you know this wasn’t a big jokey thing. We’re having a real conversation. But my default setting is comedy, and I just want to make people smile and laugh, and that’s what it’s all about. Speaking of smiling, can I do a cheesy plug?

Jameela Sure.

Simon So I was proposed a lot of things recently. I got proposed a vape campaign, a vape sponsorship, a tequila sponsorship. I was proposed by the media to lie about Meghan Markle. I said, “No,” I’m finally doing the right

Jameela This was when you were asked to lie and say that you shagged her for $75,000 and you were broke.

Simon I was broke. That’s when we were friends and I was broke, and I needed the money and I just felt sick to my stomach. And I said “No,” and she wrote me a handwritten letter thanking me that I framed. And it was really her handwriting. I found out later, and I remember getting in my P.O. Box in the desert from the Duchess of Sussex and the House of Windsor. What is this? And she wrote me from her and her husband, Henry. Harry?

Jameela Harry.

Simon Harry. He’s the queen. He’s the king, and he’s the king? He will be? Anyway.

Jameela He’s the king.

Simon And they wrote to me, “Thank you for doing the right thing. Thank you for doing the right thing, Simon.” It moved us to tears and I was like, “Oh, that’s so beautiful.” And I was like, “I’m going to keep doing the right thing.” So this is a long winded way of saying, I started a skincare line and I’m gonna give you one and it’s for men, but when we can use it too. And it’s basically, um, just because I’m always in the past using my girlfriend’s moisturizer and face wash and they get annoyed. So when I was proposed to do something positive, albeit a vain thing about having your face be moisturized, I wanted to do something to help men glow. So I started this company Mox. I’m going to give you a box. And it’s just this men’s skincare line that’s coming out soon. So there it is. That’s it.

Jameela Yeah.

Simon So it’s for you, actually give it to James.

Jameela Sure I will. If everyone sees him glowing at his show on Friday, you’ll know why. Um, so

Simon So, Mox skincare, it’s positive.

Jameela Hahaha! Yeah, you’re turning down money that you feel like isn’t putting down, putting positive things out into the world. I also really love that you came out and said that because the amount of lies that were being spread about her in that time were really wild. And you exposed the, the, the lengths to which people were going to spread those lies. And I think it’s important that, you know, people understand that that’s what women in media especially handle is this kind of shaming and the way they try to, like, use sex or nudity, not just to shame women, to shame everyone, as you learned. But, um, it’s so prevalent and it’s so grotesque that someone would try and bribe you to do a kiss and tell. I’m really glad you didn’t. And I think the universe has rewarded you.

Simon Yeah, I feel like that, it just felt, I really felt sick to my stomach when I was proposed that. I’m like, I” can’t do that.” And it kind of just put me on this path of being like, uh, just I really, truly just want to, like, do the right thing. In the past, I’ve sort of been not giving a fucking and Dirt Nasty, and I don’t care and my, I care, you know. But but it’s interesting I also I care because I still kind of don’t care. It’s a weird conundrum. It’s a weird paradox.

Jameela You care, but your life doesn’t depend on it, and you know that now.

Simon Yeah.

Jameela I’m really proud of you.

Simon Thank you.

Jameela I’m really happy for you.

Simon I’m really proud of you.

Jameela But I do, I can’t tell you, like, how much I saw this for you.

Simon Thank you.

Jameela I had a feeling you would always have your kind of McConaissance.

Simon Oh, I like that.

Jameela I remember I always used to tell, I used to tell you that. I was like, “You need one of those. You need a McConaissance.”

Simon Yeah.

Jameela Where he went from suddenly being not taken seriously

Simon To the best.

Jameela To having the coolest career in the world, but I’m also really proud of the work that you’ve done. I can’t lie, it’s really cool to see how much both of us have calmed down.

Simon Yes.

Jameela And I’m glad that we still know each other.

Simon Me too, very thankful.

Jameela Cause we witnessed each other at like a really weird time.

Simon Yeah.

Jameela And it’s nice to no longer be in that place. It’s it’s, I really was like, I just started recovering from my nervous breakdown around the time that we became friends. Um, so it was a really vulnerable moment. And it’s nice for me to have that you as a kind of bookmark of that moment to be like, “Okay, that was, things have really changed.” And it means that if that if those low lows come again, I will find my way back out.

Simon That’s right.

Jameela But yeah, I’m really, I’m really happy for you.

Simon Thank you, it means a lot, and I know you always did believe in me and I and I don’t, that doesn’t go unnoticed. It’s, not too many people out there did, and thank you.

Jameela It’s so great. I can’t believe I’m interviewing you about your fucking amazing movie career, and you’re winning crazy awards.

Simon Life is a trip.

Jameela I could never, I could, I could, I’m so happy that that actually ended up happening.

Simon Me too.

Jameela I didn’t know if either of us were going to have careers. I hoped for both of us, but

Simon Yeah.

Jameela What a mad life?

Simon What a mad life?

Jameela Simon Rex, you’re dream.

Simon Thank you so much for having me.

Jameela Lots of love. Thank you so much for listening to this week’s episode. I Weigh with Jameela Jamil is produced and research by myself, Jameela Jamil, Erin Finnegan, Kimmie Gregory, and Amelia Chappelow. It is edited by Andrew Carson, and the beautiful music that you are hearing now is made by my boyfriend, James Blake. And if you haven’t already, please rate, review, and subscribe to the show. It’s such a great way to show your support and helps me out massively. And lastly, at I Weigh we would love to hear from you and share what you weigh at the end of this podcast. Please email us a voice recording, sharing what you weigh at iweighpodcast@gmail.com. And now we would love to pass the mic to one of our listeners.

Listener I weigh my dog. I have an old retired black dog and she’s been such a lovely companion during that time where I’m working from home. I’m one of the many women in the United States and worldwide that deals with ADHD. Um, it’s been really hard to focus. Uh, having my dog by my side helps me to feel really grounded and helps me smile. And this podcast. Thanks.