20 Great Episodes of Conan O’Brien Needs a Friend Prior to 2020 Conan O'Brien is a legendary comedian and internet innovator

Conan Christopher O’Brien is a one of the greatest comedy hosts of all time and one of my personal favorites. I’ve watched Conan since the 12am time slot doing staring contests with Andy Richter. Conan finally worked his way to his dream gig hosting The Tonight Show before contract disputes left him unable to work.

I saw Conan on his Legally Prohibited from Being Funny on Television Tour, and it was fantastic. It’s where I was introduced to Reggie Watts, saw Conan’s guitar chops, and really enjoyed the full experience. His drummer Max Weinberg was one of the famous musician friends of my high school band teacher, Coach Rick Klein, down at Buena High School. Their performing art center is now named after Coach.

Conan worked on Saturday Night Live and The Simpsons before joining the talk show circuit, and he kept an eye on digital when he returned to TV on TBS. Team Coco and his digital efforts kept him relevant much longer than his childhood heroes.

What’s great about the podcast that you don’t get on the show (although his self-deprecating skits do touch on it) is his mistreatment of his personal assistant Sona Movsesian and producer Matt Gourley. Their banter is better than what his relationship with Andy Richter has evolved into over the years.

The first awkwardly read World of Warcraft commercial you hear (and his mispronunciation of ADD) will keep you hooked.

Listen to these 20 great episodes of Conan’s podcast, where he sits down and gets even deeper with his celebrity guests with behind-the-scenes stories that show he’s a force to be reckoned with in the 2020s.

20. Pete Holmes

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Pete Holmes

Pete Holmes is one of the most down-to-earth and genuine comedians in the game. His laugh is great, his asides are always chuckleworthy, and his energy is always manic. He feels like that guy in class that’s just trying to hard to be funny, but he’s actually funny.

19. Ron Funches

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Ron Funches

Ron Funches is one of Conan’s guests who’s probably the most honored to be his friend. He’s in love with The Rock and has one of the best Conan on guitar stories on the planet. Someone hug this teddy bear of a man.

18. Michelle Obama

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Michelle Obama
FILE – In this Dec. 19, 2018 file photo, former first lady Michelle Obama responds to questions as she is interviewed by actress Sarah Jessica Parker during an appearance for her book, “Becoming: An Intimate Conversation with Michelle Obama” at Barclays Center in New York. Obama has postponed an appearance in Tacoma, Wash., on Friday night, Feb. 8, 2019, over concerns about an impending snowstorm in the Northwest. The Tacoma Dome says the appearance to promote her memoir, “Becoming,” has been rescheduled for March 24, 2019. (AP Photo/Frank Franklin II, File)

O’Brien’s following of Maron’s WTF footsteps took him to Barack’s wife for a great conversation. She gets real on issues without coming off as a soapbox.

17. Dana Carvey

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Dana Carvey

Dana Carvey is a comedy legend, and O’Brien uses him to show off how long these interviews really are. The extended deep dive that ended the 2019 season gave us all a look at what he has to work with. I can’t wait to hear everything Conan has in his deep archives.

16. Adam Sandler

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Adam Sandler

Adam Sandler is notoriously shy, and anyone would kill to be a fly on the wall of this conversation. He basically broke the internet with this interview, although their closeness did make the episode almost too polished. In a post-WTF world, we’re always wanting more from a guy like Sandler.

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15. Nicole Byer

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Nicole Byer

Nicole Byer is a treasure, and she brings out the best of everyone in the room. She’s part of a wave of positive comedians, and it blends perfectly with Conan’s self-deprecation. Byer’s completely effortless in her delivery.

14. Bob Newhart

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Bob Newhart

Bob Newhart had a crispy clean image back in the day when TV dads needed that. But Bob Saget changed the game, and elderly Newhart typically shows up in cameos to talk shit to someone. He does it to Sheldon on Big Bang, and he does it to Conan here. Conan is the perfect punching bag, making this a classic episode forever.

13. Stephen Colbert

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Stephen Colbert

Stephen Colbert is another legend of late night comedy, and, as you can imagine, the conversation between these two is AMAZING. Colbert goes for the dark side and shows some of his demons to help Conan get his online buzz. You can tell everyone’s got a stake in making this podcast work.

12. Wanda Sykes

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Wanda Sykes

Wanda Sykes is a short episode, but she does work well as the alpha compared to O’Brien’s beta. She’s a bit bored, but it shows what this format is capable of. Obviously he wanted to get some diversity in his lineup, and Sykes is the one to do it. If only she wanted to be O’Brien’s friend.

11. Patton Oswalt

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Patton Oswald on Stage

Patton Oswald’s comedic style is a perfect blend for Conan. And this episode has the same warmth as Kristen Bell. This is a great episode to get to know both of these men.

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10. Lin-Manuel Miranda

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The ensemble conversation is what starts to build in this cast with Lin Manuel Miranda. It opens the show format with an interview, but then Conan makes it his own with the zany improv that made him so beloved in the first place.

9. Kristen Bell

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The Good Place Clowns

Kristen Bell is a delight to watch on screen and in interviews. She talks to Conan about the troubles of parenting, keeping positive to make the kids kinder, and a LOT about her husband Dax Shephard. He has his own podcast we’ll discuss in a bit.

8. Kumail Nanjiani

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Kumail Nanjiani

Kumail Nanjiani no-showed to a few podcasts, but he shows up to Conan’s. You can definitely see him flexing his muscle on this one, and Gourley really comes into his own as a character. His talk of failing as a godfather and driving his niece to the occult is great.

7. Julia Louis-Dreyfus

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Julia Louis Dreyfus

Speaking of Dax Shephard’s Armchair Expert podcast, Julia Louis-Dreyfus is a great interview. Conan has to work hard to keep it from becoming a clone, but you can see he’s a seasoned interviewer now. Still, it sticks out that Conan is really letting his guests stick to their scripts without challenging them much. One can only wonder how it’ll develop over time.

6. Bill Hader

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FYC Event For IFC's "Brockmire" And "Documentary Now!" - Inside
NORTH HOLLYWOOD, CA – MAY 31: Actor Bill Hader speaks onstage during the FYC event for IFC’s “Brockmire” and “Documentary Now!” at Saban Media Center on May 31, 2017 in North Hollywood, California. (Photo by Matt Winkelmeyer/Getty Images)

Sometimes a conversation with Conan is just a chance to have fun and laugh. Bill Hader keeps the energy positive, and it’s a massive departure from what you’re used to hearing in the seriousness of other podcasts.

5. Andy Richter

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Conan and his sidekick go head-on into discussions of what it’s like having a day-to-day job on the show. No, they don’t sleep together. Yes, they are their own men. And when the cameras are off, the banter between the two takes on a much more serious tone as they look back on two storied careers.

4. Howard Stern

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Howard Stern

Howard Stern is a radio veteran, and his inclusion on this podcast shows the celebrity muscle Conan can flex with his decades in the business. The two have a camaraderie during this sit down as they discuss the affects of fame on mental health, being criticized for your creative output, and more. Stern jumps it off with a confrontation about how they’re not friends (and admitting his insecurity about O’Brien’s Harvard pedigree), and you can hear them become friends as the conversation goes on. Their admission that they are who they are because of who they were in the 20th century.

3. Jimmy Kimmel

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If there’s one thing Conan knows a lot about, it’s the late-night talk show game. This discussion with Kimmel shows two amazing perspectives of the game. It’s telling that Conan has yet to have his Tonight Show Replacement on yet. There are still a lot of legends of late night comedy for him to tap in the 2020s.

2. Marc Maron

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WTF with Marc Maron Podcast

Maron is the guy whose podcast paved the way for Conan to bring his comedy to a new generation. Of course Maron wants to know why he’s never been on The Tonight Show, and Conan’s frank response is it’s too short. In a way, it’s like listening to Maron pass the torch to an O’Brien who may be going full digital in 2022.

1. Will Ferrell

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Will Ferrell COnan

O’Brien kicks his podcast off with a bang. If you’re not already familiar with Ferrell’s lengthy legacy with the show, he was always the clutch guest who came out with a crazy skit. Initially many involved him getting into an argument with himself in the audience and then being attacked by a stuntman that looks nothing like him (black guy, midget, etc). And Ferrell


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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