Legendary television host David Letterman has endless admiration for Conan O’Brien. David joins Conan to kick off season two with a conversation about David’s unmatchable career in late night, interactions with Johnny Carson and Bob Hope, what they see for their kids in the future, and why the best people in showbiz are always the hardest working. Plus, Conan gives an update on the horse David gifted to him, and Conan’s assistant Sona and producer Matt Gourley join in for another round of Review the Reviewers.

Writer, comedian, and actress Tina Fey feels good about being Conan O’Brien’s friend; it tracks. Tina and Conan sit down to discuss SNL-induced OCD, bringing Mean Girls to Broadway, husband Jeff Richmond’s mysterious recurring Conan role, getting over the “chipple,” and improvising like a writer. Plus, Conan responds to a voicemail about which president he’d like to eat.

Comedian and host of Last Week Tonight John Oliver feels cautiously optimistic about being Conan O’Brien’s friend. John and Conan sit down to chat about being nominated for an OBE, the silliest ways they’ve spent their show budgets, why the U.S. got the best of British comedy, performing with the Cambridge Footlights, and why John can never watch The Great British Baking Show. Plus, Conan gets a lesson in printer etiquette from his staff.

Actor and comedian Zach Galifianakis feels cautious about being Conan O’Brien’s friend. Zach and Conan sit down to talk about the showbiz cult of ego, mining comedy from miscommunication, phone calls from the president, hunting for clay, and being inspired by a professional whistler. Later, Sona and Matt Gourley surprise Conan with a Halloween treat.

Music legend Neil Young feels good about being Conan’s friend. Neil and Conan sit down to talk about Neil’s 1957 Eldorado Biarritz, why he won’t allow his songs in commercials, the importance of preserving musical sound quality, recording his new album Colorado with Crazy Horse at 9,200 ft elevation, and what Neil loves about his Gretsch White Falcon guitar. Plus, Conan and his staff conduct a Gerber taste test.

Actor Paul Rudd feels excited about Conan O’Brien’s friend. Paul and Conan sit down to talk about Paul’s long-running “Mac and Me” gag on Conan, the urge to go out of bounds, showbiz muscle memory, and learning how to bartend. Later, Conan and his team respond to a listener voicemail about being scared.

Comedian, television host, writer and producer Ellen DeGeneres feels honored to be Conan o Brien’s friend. Ellen and Conan sit down to talk about wearing gold jackets in the 80s, Ellen’s return to stand-up after 15 years with her special Relatable, the pressures of maintaining a talk show persona, and the importance of not taking things so seriously. Plus, Conan contemplates his own name while dropping others in response to a listener’s email.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Actor, producer, and writer Paul Reubens feels fantastic about being Conan O’Brien’s friend. Paul and Conan sit down to talk about wanting to join the circus, the letter Paul wrote to Walt Disney, remembering Phil Hartman, and anxiety over getting recognized. Later, Conan and Sona go head to head with a podcast pop quiz.

Actor Will Arnett feels pretty put out about being Conan O’Brien’s friend. Will and Conan sit down to talk about being known as a voice-over artist, the best bits of Brian McCann, and finding his crowd with Arrested Development. Plus, Conan and Sona take another swing at a Podcast Quiz.

Comedian and actress Whitney Cummings feels stressed out about being Conan O’Brien’s friend. Whitney and Conan sit down to talk about being a serious child, impetigo and epigenetics, and the stresses of planning a wedding. Later, Conan hears about his assistant Sona’s medical procedure.

Comedian and actor Steve Coogan feels quietly optimistic about being Conan O’Brien’s friend. Steve sits down with Conan to talk about channeling comic persona Alan Partridge, Steve’s newest film Greed, portraying Stan Laurel in Stan & Ollie, and not minding when someone doesn’t think he’s funny. Plus, Conan and his team look back on Conan’s technological achievements with a special montage.

Actress D’Arcy Carden feels hopeful about being Conan O’Brien’s friend. D’Arcy and Conan sit down to talk about bringing Janet to life on The Good Place, meeting her comedic heroes, babysitting for Bill Hader, and being rewarded for working hard and not asking too much. Later, Conan takes a look at an old college photo with his team.

Comedian and actor Kevin Nealon feels confused that he’s considered Conan O’Brien’s friend. Kevin and Conan sit down to talk about working on the Hans & Franz musical, perfecting the interview on his YouTube show Hiking with Kevin, and planning a road trip. Plus, Conan gives out much-needed advice on dating and getting along with family during quarantine.

Comedian, actor, writer, producer Ricky Gervais feels strangely underwhelmed about being Conan O’Brien’s friend. Ricky sits down with Conan to discuss getting a laugh out of the worst of humanity, the upcoming season of his Netflix show After Life, and finding out his heroes are just regular people. Plus, Conan shares what he’s learned about tech in the days of quarantine.

Nick and Conan sit down to talk about how being a late bloomer informed the making of Big Mouth, collaborating with longtime partner John Mulaney on Oh, Hello: the P’dcast, and finding positives within a long stretch of quarantine. Later, Conan and his team answer listener questions about homeopathic remedies and more.

Actor Ted Danson feels oddly comforted about being Conan O’Brien’s friend. Ted and Conan sit down to talk about false humility, being recognized (while wearing a mask), and pandemic farts. Plus, Conan shares a touching clip from the set-up of the remote recording.

Actor Mike Myers feels prehensile about being Conan O’Brien’s friend Mike sits down with Conan to talk about treating the audience as the boss, sharing his iconic comedic filmography with his kids, and the “cinema bleak” of Canada. Later, Conan gets frantic with a one-off segment titled “Maybe I’m As Big a Nerd As Gourley”.

Filmmaker J.J. Abrams feels exceedingly lucky about being Conan O’Brien’s friend. J.J. sits down with Conan to discuss finding the confidence to take the reins on iconic franchises like Star Trek and Star Wars, how to cut together a good trailer, and getting his first gig writing the music for the 1982 horror film Nightbeast. Later, Conan considers his approach to ad reads as he and his team Review the Reviewers.

Comedian Russell Brand feels nervous about being Conan O’Brien’s friend. Russell and Conan sit down to talk about the appearance of the sacred within the ordinary, making pain lucrative, and the constant of late-night talk shows in America. Later, Conan answers a listener question about which member of his team he would fire.

Actor Rob Lowe feels optimistic about being Conan O’Brien’s friend. Rob and Conan sit down to talk about advice from Cary Grant and Paul Newman, what’s in store with Rob’s new podcast Literally! With Rob Lowe, and which Supreme Court justice Rob considers a friend. Plus, Conan reviews submitted pieces of risqué fan art.

Comedian Amy Schumer feels fully indifferent about being Conan O’Brien’s friend. Amy and Conan sit down to talk about comedians getting buff, cult leaders, debuting Amy Schumer Learns to Cook, and whether a baby can have “it”. Plus, Conan and his team celebrate the culmination of their second season with some parting thoughts.

On the first installment of a special Summer S’mores series, Conan and his team loosen up by sharing memories of summers past.

Conan’s team tries to induce chill-ness by any means necessary on another special Summer S’mores episode.

Conan and his team contemplate an alternate presidential history on another Summer S’mores special.

Actor Tom Hanks feels grand about being Conan O’Brien’s friend. Tom sits down with Conan to talk about recovering from COVID-19 in Australia, writing the screenplay for his new WWII-era film Greyhound, and the first thing he ever saw on YouTube.

Conan gives the Chill Chums some friendly criticisms during another Summer S’mores special.

On another Summer S’mores special, Conan and the Chill Chums discuss the perfect murder.

On the final Summer S’mores special, Conan and the Chill Chums discuss who Conan should expect to see at his own funeral.