Comedian Ali Wong feels very new about being Conan O’Brien’s friend.

Ali and Conan sit down to talk about her father’s love of pajama pants, why travel is the hardest part of stand-up, the mysterious metrics of Netflix, and maintaining her strong sense of Asian-American identity. Plus, Conan talks to his assistant Sona about getting caught breaking the rules at Disneyland.

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Comedian Jim Gaffigan feels like Nikki Glaser felt about being Conan O’Brien’s friend.

Jim and Conan sit down to talk about showbiz friendships, the power of bragging, drinking options, and presidential endorsements. Later, Conan recalls an overreaction to a home emergency.

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Writer/director/producer Judd Apatow does not feel hopeful about being Conan O’Brien’s friend.

Judd sits down with Conan to talk about using silence in their work, lifting up comedy stars like Seth Rogen and Pete Davidson, fashion tips from Jon Lovitz, reminiscing about eating, and comic rhythm. Plus, Conan and Sona dish on producer Matt Gourley in his absence.

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Actor Keegan-Michael Key feels overwhelmed about being Conan O’Brien’s friend.

Keegan and Conan sit down to chat about growing up a 60s guy (in the 80s), favorite niche impressions, performing sketch alongside President Obama, and discovering entertainment as a career path. Later, Conan responds to a listener voicemail about socks.

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Comedian Sarah Silverman feels grateful about being Conan O’Brien’s friend.

Sarah and Conan sit down to chat about first times, getting aggressively dumb and silly, lessons from Garry Shandling, and the fear of speaking up. Plus, a listener voicemail forces Conan to contemplate a sandwich that bears his name.

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Actor, author, and playwright Jesse Eisenberg feels desperate to be Conan O’Brien’s friend.

Jesse and Conan sit down to discuss the better ways of humbling oneself, being driven by anthropological curiosity, avoiding online negativity, and the odd homogeneity of Los Angeles. Later, Conan attempts to inspire a pregnant listener as he and his team Review the Reviewers.

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Actors, writers and comedians Eugene Levy and Catherine O’Hara feel absolutely delighted, flattered, and honored to be considered Conan O’Brien’s friends.

Eugene and Catherine sit down with Conan to talk about taking chances in the pre-internet era with SCTV, transforming into the characters they play on Schitt’s Creek, the formula that makes a successful comedy show stick, and legendary tales from the Second City stage. Later, Conan takes it up with the Cheesecake Factory menu.

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Comedian Nikki Glaser feels overwhelmed about being Conan O’Brien’s friend.

Nikki and Conan sit down to discuss modern perspectives on the vagina, the emotional toll of performing a roast, how discovering stand-up comedy helped Nikki manage an eating disorder, and going down in flames with her worst-ever jokes told at a wedding. Plus, Conan responds to the idea of his name on a rump-cheek as he and his staff Review the Reviewers.

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Basketball legend Charles Barkley feels great about being Conan O’Brien’s friend.

Charles and Conan sit down to chat about the extreme competition of going pro, getting booed offstage at a Katy Perry concert for dissing the Timberwolves, his friendship with Shaq, and advocating for education. Later, Conan issues a warning to his staff about spoiling certain tv shows.

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Author, comedian, and former senator Al Franken is already a f***ing friend of Conan O’Brien’s.

Al and Conan sit down to talk about favorite SNL sketches that never made it to air, doing ‘The Brain Tumor Comedian’ with Tom Davis, shutting down George Harrison’s drunken piano playing, and the jokes that failed to land with guests of The Al Franken Podcast. Plus, Conan follows up on the resurfacing of his correspondence with iconic writer E.B. White.

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Author and journalist Malcolm Gladwell feels pressured into being Conan O’Brien’s friend.

Malcolm and Conan sit down to talk about Malcolm’s new book Talking to Strangers: What We Should Know about the People We Don’t Know, conversations about gardening, tabloid inventions, tales from the IRA, and Conan’s own special cult of personality. Plus, Conan and his assistant Sona engage in a struggle for power.

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Comedian John Mulaney feels falsely modest about being Conan O’Brien’s friend.

John and Conan sit down to talk about growing up in a family trapped in the 1950s, the power of dressing well, fulfilling a lifelong dream of a career in comedy, and the rewarding experience of creating his new Netflix show John Mulaney & The Sack Lunch Bunch. Later, Conan and his team share their formative cinematic experiences.

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Actor/musican Jack Black feels shitty about being Conan O’Brien’s friend.

Jack and Conan sit down to talk about the 1999 pilot Heat Vision and Jack, laying down hot tracks with Jack White, bringing the energy to max performing with Tenacious D, the greatest mobile golf game, and the later films of Ruth Gordon. Plus, Conan issues another State of the Podcast address.

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Former First Lady and Secretary of State Hillary Clinton and daughter Chelsea Clinton feel great (but a little apprehensive) about being Conan O’Brien’s friends.

Hillary and Chelsea sit down with Conan to discuss the stories that inspired them to co-write The Book of Gutsy Women, Chelsea’s teenage years in the White House, unusual Halloween costumes, the incredible pace of technology, and why we should never quit betting on optimism. Plus, Conan spins an alternate history of Idaho in response to a listener’s voicemail.

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Comedy icon Eric Idle feels moderately aroused about being Conan O’Brien’s friend.

Eric and Conan sit down to talk about his autobiography Always Look on the Bright Side of Life, playing ukulele with George Harrison, Monty Python’s genesis at Cambridge, finding a fan in Elvis Presley, the Fab Four’s response to parody group The Rutles, and looking back on fifty years of Python. Plus, Conan makes an effort to help his assistant Sona manage her side hustles.

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