Side-Splitting Facts About Conan O'Brien

April 4, 2018 | Danny Bianco

Side-Splitting Facts About Conan O'Brien

He’s entertained as a writer on Saturday Night Live and The Simpsons as well as being a late night host for over twenty years. But how much do you really know about the zany red-headed man they sometimes call Coco? Here are 42 side-splitting facts about Conan O’Brien.

Conan O'Brien Facts

42. Influences

One of O'Brien's major influences was Tonight Show host Johnny Carson. On Fridays, his dad would let the young O'Brien stay up to watch Johnny Carson’s monologue. O’Brien was also strongly influenced by Warner Brothers cartoons and SCTV.

Conan O'Brien factsWikimedia Commons, Gage Skidmore

41. Our Man in Havana

In 2015, O'Brien took the crew of his show to Cuba to tape a series of remote segments there. This was the first time that any late night television host had taped a show in Cuba since Jack Paar taped The Jack Paar Tonight Show in Cuba in 1959.

Conan O'Brien factsConan (TV Series) Conan in Cuba (2015), Conaco

 40. Red Headed Cousins

O'Brien is a third cousin of fellow New England comedian and actor Dennis Leary.

Conan O'Brien factsWikimedia Commons

39. Not the First Choice

When David Letterman left the Late Night franchise at NBC for his own show at CBS in 1993, the first choice for a replacement host was Dana Carvey, not O’Brien. Carvey would turn down NBC’s offer and instead go on to host his own comedy show, The Dana Carvey Show, in 1996.

Conan O'Brien facts Wikimedia Commons


38. First Audition

When O'Brien first auditioned for the role of host of the new Late Night show, he did so on the set of The Tonight Show with Jay Leno. O’Brien’s audition guests were Jason Alexander and actress Mimi Rogers. It is reported that Jon Stewart, Drew Carey, and Paul Provenza also auditioned, but were rejected in favor of O'Brien.

Conan O'Brien factsLate Night with Conan O

37. Tough Critic

Following the airing of his first Late Night show, the New York Times Opinion section contained a negative review of the show titled “O’Brien Flops!” by a curious source. Who was it? O'Brien himself, of course! The article concluded by stating “As much as this writer would like to root for Mr. O'Brien, one can't help but have grave doubts about his prospects.”

Conan O'Brien factsLate Night with Conan O

36. Bad Omen

On his first day at work writing for The Simpsons, O'Brien was led to his office and left to begin working on show ideas. After working for a few minutes, he left his office for a drink of coffee. Soon thereafter he heard a large crash and went back to his office where there was a hole in the window and a dead bird on the ground. Auspicious beginnings, indeed!

Homer Simpson FactsThe Simpsons, 20th Century Fox Television

35. Made of Clay

In 2003, there was an episode of Late Night with Conan O’Brien that was entirely done using Claymation. The guests for this show included Johnny Knoxville, Richard Lewis and David Bowie.

Conan O'Brien factsLate Night with Conan O

34. Lucky Break

When O'Brien quit his job as a writer for SNL in 1991, he had nothing else lined up nor did he have any idea what he was going to do. O’Brien states: “I had no plan whatsoever. I was literally in this big transition phase in my life where I decided, I'll just walk around New York City, and an idea will come to me.” Soon afterwards, The Simpsons called and offered O’Brien a writing job. O’Brien credits The Simpsons with saving his professional career.

Conan O'Brien factsWikipedia


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33. Gonzo TV

O'Brien reached out to the famous gonzo author Hunter S. Thompson for years seeking to get him on his show. Thompson always refused until provisionally accepting O'Brien's offer on one condition: that O'Brien and crew fly up to Thompson’s farm in upstate New York and shoot the segment remotely from the farm and that O'Brien and Thompson will shoot guns and drink hard liquor. O'Brien agreed and filmed a riotous segment where a liquored-up O'Brien shot the NBC peacock with a machine gun.

Famous Best Friends factsWikimedia Commons


 32. A Genuine, Bona-Fide Electrified Six Car Monorail

O’Brien’s most famous writing credit for The Simpsons is probably the episode “Marge vs. the Monorail,” where the City of Springfield is tricked by a dashing con-man into purchasing an expensive and dangerous monorail. O’Brien first conceived of the concept of the episode when he saw a billboard in L.A. with the word “Monorail” on it with no other details or explanation. O’Brien has stated that the episode is his favorite of all episodes he wrote for the show. The episode frequently ranks among the top episodes the iconic show has ever made.

Conan O'Brien facts The Simpsons (1989– ), 20th Century Fox Television

31. Random Follow

Conan O’Brien only follows one person on Twitter. That person? A fan named Sarah Killen who he decided to follow at random one day soon after joining the site. O’Brien followed Killen in 2010 when she had 3 followers. Since O’Brien’s fateful follow, Killen currently stands at over 400k followers!

Music Industry factsPxfuel

30. A Nose for Trouble

Would you believe that O’Brien’s nose is not the one he was born with? It’s true. But it’s not because he sought out cosmetic surgery. In an interview on Marc Maron’s WTF podcast, O’Brien admitted that he was attacked by a youth street gang when he was in high school and was beaten to a pulp. O’Brien explains that at the emergency room he asked the doctor if his nose was broken and the doctor retorted: “Broken? Good god, man, it's a bag of bones!”

Will Ferrell factsGetty Images

29. Eminent Domain

In a 2006 Late Night skit, O'Brien riffed that one of the show’s band members was viewing a website located at “” As a measure to limit the company’s liability, NBC immediately purchased the domain name for a cool $159. O’Brien writers soon extended the joke by transforming into a real website that was soon visited by more than 3 million fans of the show.

Conan O'Brien factsLate Night with Conan O

28. Stalker

Beginning in September 2006, O’Brien was stalked by a Roman Catholic priest named David Ajemian. The issue began as a result of the priest’s frustration at being denied entry into the audience of a Late Night taping. Ajemian sent O’Brien a series of threatening letters and once attempted to forcefully enter a Late Night taping, before being arrested.

Great Escapes Facts PxHere

27. Generous Man

When O'Brien was bought out of his Tonight Show contract by NBC in a $45 million deal, about 50 staffers received absolutely nothing as part of the deal. Generous O’Brien paid these staffers six weeks severance pay out of his own pocket.

Conan O'Brien factsThe Tonight Show with Conan O


26. Ordained Host

Did you know O’Brien is an ordained minister and performed a same-sex marriage that was broadcast on his show? That’s right, O’Brien specifically became ordained in order to perform the marriage between a member of his staff and their partner while taping the show in New York City.

Conan O'Brien factsConan (2010– ), Conaco

25. Little Drummer Boy

O’Brien played drums while a student at Harvard. One of his classmates, Damon Krukowski, was in a band at the time but lacked his own drum kit and borrowed O’Brien's. Krukowski’s band happened to be Galaxie 500, a very influential dream-pop band from the late 1980’s and early 1990’s. One can hear O’Brien’s borrowed drum kit on the band’s first album.

Conan O'Brien facts Wikimedia Commons

24. D’Oh

While writing for The Simpsons, O’Brien would sometimes create a character that he called the “Nervous Writer” in order to get a laugh out of the writer’s room. The character would anxiously open a can of Diet Coke, spraying it all over himself, and then attempt to pitch a joke.

Conan O'Brien factsShutterstock

23. Pay to Play

When O'Brien left The Simpsons to host Late Night with Conan O’Brien, he was still under contract with The Simpsons. The Simpsons were reluctant to let O’Brien leave and insisted that he either fulfill the terms of the contract or pay damages for breaking it. In the end, NBC agreed to pay half and O’Brien agreed to pay the other half in order to break the contract. Good thing that whole late night host thing worked out for him!

Conan O'Brien factsLate Night with Conan O


22. What About Ryan Though?

The Office cast members John Krasinski, Ellie Kemper and Mindy Kaling were all interns on Late Night with Conan O’Brien.

The Office FactsGetty Images

21. Andy’s Sister

In the early years of Late Night with Conan O’Brien, a recurring character was sidekick Andy Richter’s “sister” Stacy. The dorky, brace-wearing Stacy, who had a desperate crush on O'Brien and who flew into a psychotic rage when her advances were rejected, was played by a young Amy Poehler.

Conan O'Brien factsLate Night with Conan O


20. Running Joke

Paul Rudd is a frequent guest on all of O'Brien's late night shows. Rudd is always a hilarious guest and he has successfully pranked the talk show host's audience for the last fifteen years running. While Rudd is at O'Briens’s desk promoting his latest movie and promises to show a clip from it, he instead shows a scene from the 1988 alien movie Mac and Me depicting a wheelchair-bound child falling from a cliff.

Conan O'Brien factsConan (2010– ), Conaco

 19. Chance Encounter

O'Brien actually met his wife while filming a Late Night skit! Back in 2000, O’Brien filmed a skit at advertising agency Foote, Cone and Belding where Liza Powel was a young copywriter. O’Brien and Powel hit it off during the taping of the skit and dated for 18 months before getting married.

Conan O'Brien factsShutterstock

18. Axeing to Leave

When leaving Late Night to take over the Tonight Show, O'Brien took an ax to the Late Night set. This wasn’t a moment reminiscent of The Shining, though, as it was a means of giving the studio audience literal physical souvenirs from the set.

Conan O'Brien factsLate Night with Conan O

17. So Close, Yet So Far

The Emmys have been both kind and unkind to O'Brien. Every year from 1996 to 2013—that’s 17 years—O'Brien has been nominated for at least one Emmy award. But he’s won only one twice! Once was in 2007 for Outstanding Writing for a Comedy, Music or Variety Series for Late Night and the other time was in 2012 for Outstanding Achievement in Interactive Media for Conan.

Conan O'Brien factsShutterstock

16. Karaoke Comedian

During his 2010 comedy tour entitled “Legally Prohibited From Being Funny”O'Brien regularly played guitar and sang for the audience, performing covers of various songs. Frequently played tunes included Radiohead’s “Creep” and Gloria Gaynor’s “I Will Survive.”

Conan O'Brien factsWikimedia Commons

15. All in the Family

O’Brien comes from an intellectual family. His dad is a professor of medicine at Harvard Medical School and his mother is a lawyer and partner at a prominent Boston law firm.

Conan O'Brien factsWikimedia Commons

14. Gentleman and a Scholar

O'Brien his parents may be accomplished, he’s no slouch either. O’Brien was his high school’s valedictorian and the managing editor of his high school newspaper. O'Brien then went on to graduate magna cum laude from Harvard, majoring in history and literature.

Conan O'Brien factsGetty Images

13. Game Developer

While at Harvard, O'Brien developed a spoof of a basketball video game. In O’Brien’s spoof game, the NBA’s Boston Celtics took on a classical ballet troupe—a comedic send-up of the then-popular One-on-One game pitting Larry Bird vs. Julius Erving. Conan claimed at the time to have had a contract with game developer EA Sports to develop this idea, although it fell through.

Jeopardy FactsGetty Images

12.  Crude Comedy

While a writer on SNL, O’Brien wrote a sketch with Robert Smigel called ‘Nude Beach”. The sketch is infamous for having used the word “penis” 42 times.

Conan O'Brien factsShutterstock

11. What Could’ve Been

O'Brien wrote a TV pilot starring Adam West with fellow-writer Robert Smigel. The pilot was called Lookwell and centered around West, who played the character of Ty Lookwell: an older, washed up former action hero who is deputized in a small town and attempts to solve real crimes. While the show was never picked up by the network, the pilot episode is now revered as a cult classic!

Conan O'Brien factsShutterstock

10. Fake Feud

During the 2008 Writers Strike, O’Brien staged a fake feud with Stephen Colbert of The Colbert Report and Jon Stewart of The Daily Show. The “feud” was based on which of the three was responsible for giving Mike Huckabee’s Republican presidential campaign a slight bump in the polls. The feud ended with an “all-out-brawl” between the three comedians.

Conan O'Brien factsLate Night with Conan O

9. Conan Concussed

O'Brien suffered a concussion on-air in 2009 while running a race with guest Teri Hatcher as part of a Tonight Show skit. O’Brien slipped on the soundstage and hit his head on the floor. A dazed O’Brien then slurred his way through the dialogue going to commercial before being treated at a hospital.

Conan O'Brien factsLate Night with Conan O

8. I Didn’t Do It

O'Brien first guest appearance after getting the Late Show was on his former show, The Simpsons.O'Brien played himself in the episode “Bart Gets Famous,” interviewing Bart at the height of his fame as an accidental catchphrase comedian. The Simpsons wrote the episode after O'Brien had auditioned for the late night gig but before he had been offered the hosting job.O'Brien recorded his part soon after his show went to air but believing his late night show would be canceled before The Simpsons episode ever aired.

Conan O'Brien facts The Simpsons (1989– ), 20th Century Fox Television

7. Two-Time Host

O'Brien hosted the White House Correspondents Dinner in 1995 when Bill Clinton was President and then again 18 years later in 2013 when Barack Obama was President.

Conan O'Brien factsGetty Images

6. Risky Business

During the first few years at Late Night, O’Brien was at constant risk of cancellation. Critics viewed him unfavorably, seeing him as nervous and intellectual and even too tall to succeed. At one particularly low point in 1994, NBC executives threatened to put O’Brien on a week-to-week contract.

Conan O'Brien factsLate Night with Conan O

5. College Clown

Once, when he was the editor of Harvard’s comedy paper, The Harvard Lampoon, O’Brien was arrested after stealing an entire shipment of the regular Harvard newspaper, The Harvard Crimson. Coincidentally—or perhaps not—the editor of the Crimson at the time was Jeff Zucker, who later ended up in charge of NBC when the decision was made to replace O’Brien with Jay Leno on the Tonight Show.

Conan O'Brien factsGetty Images

4. Pranking Cosby

When O’Brien was 19, he pulled a prank on none other than Bill Cosby. While a student at Harvard, O’Brien was keen to meet one of his comedy idols and hatched a positively devious plan to do so. O’Brien contacted Cosby, claiming that he was being awarded a lifetime achievement award from Harvard and needed to fly to the school to accept it. Cosby bit O’Brien’s bait and arrived at Harvard by private plane all in order to be picked up by O'Brien in his parent’s station wagon and presented with an old bowling trophy as an award!

David Letterman factsGetty Images

3. Prankster

While a college student at Harvard, O'Brien pranked both the local and state police at the same time. O’Brien and a group of friends rented a jackhammer and dressed as construction workers. O’Brien then called the Boston police and told them college students illicitly dressed as construction workers were jackhammering the street.O'Brien then called the state police and relayed that college students dressed as policemen were harassing a group of construction workers, in order to get the state police to arrest the local police!

Barack Obama factsPixabay

2. Men Without Tights

O’Brien’s pranking also includes the time he masterminded the theft of Robin’s tights in the 1980s. That’s right. Burt Ward, who played Robin on the Batman TV series, spoke at Harvard in the ‘80s and brought along his famous Robin suit. During his speech, Harvard Lampoon pranksters, including O’Brien, dressed up as security guards and stole the suit. They prank-called Ward afterward pretending to be various Batman villains before giving the suit back.

Conan O'Brien factsBatman (1966–1968), 20th Century Fox Television

1. Don’t Flatter Me

In the early 1990s, O’Brien was briefly romantically involved with Lisa Kudrow, who went on to significant fame playing Phoebe on the hit TV show Friends. Kudrow convinced O’Brien that he should begin performing comedy as well as writing it. O’Brien, who was content as a comedy writer, disagreed with Kudrow, saying that she was being overly flattering.

Conan O'Brien factsLate Night with Conan O

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30

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