Although Conan O’Brien was once a Letterman wannabe, he truly came into his own. After 14 successful seasons of Late Night with Conan O’Brien and less than one season of The Tonight Show with Conan O’Brien, he went from a virtual unknown to one of the cornerstones of late-night comedy.
He entertained people as a writer on Saturday Night Live and The Simpsons before becoming a talk show host, but there are so many things people don’t know about the zany redhead. From his iconic hairstyle to his surprising educational background, these side-splitting facts will make you see Conan O’Brien in a whole new light.
Family of Brains
Born and raised in Brookline, Massachusetts, Conan O’Brien was raised by two brilliant parents. His father, Thomas O’Brien, is a physician, epidemiologist, and professor of medicine at Harvard Medical School. Meanwhile, his mother, Ruth O’Brien, is a retired attorney and former partner of a big law firm in Boston.
O’Brien’s parents instilled strong academic values in him, so he served as the managing editor of his school’s newspaper and interned for a congressman during his sophomore year. People knew he had writing talent because, during his senior year, O’Brien won the National Council of Teachers of English writing contest for his short story.
An Ivy League Genius
After graduating as the valedictorian of his high school class, O’Brien attended Harvard University. He studied history and literature and graduated magna cum laude with a Bachelor of Arts degree in 1985. While he was there, he briefly played drums in a band called the Bad Clams and wrote for The Harvard Lampoon.
While writing for The Harvard Lampoon, O’Brien developed his comedy writing skills and created a spoof of the video game One on One: Dr. J vs. Larry Bird, in which the Boston Celtics play against a ballet troupe. He eventually served as the president of The Lampoon. His future boss at NBC, Jeff Zucker, was the president of the Harvard newspaper at the same time.
His First Big Job
Right after college, O’Brien moved to L.A. and started writing for HBO’s Not Necessarily the News. After two years of working at HBO, he was hired as a writer for Saturday Night Live because executive producer Lorne Michaels was interested in his skills. He also performed with an improv group during this time.
Although he was only at SNL for three years, O’Brien wrote recurring sketches as “Mr. Short-Term Memory” and “The Girl Watches.” In 1989, he and his fellow SNL writers received an Emmy for Outstanding Writing in a Comedy or Variety Series. He also occasionally appeared as an extra in sketches.
The Simpsons Save O’Brien’s Career
In 1991, Mike Reiss and Al Jean, then showrunners of The Simpsons, called O’Brien and offered him a job as a writer. It was considered a prestigious position in the writing community, and it saved his career. He was the first hire after the show’s original crew, and everyone wanted that position.
O’Brien had just quit his job with Saturday Night Live, and he had no other work lined up. It was a huge transition period in his life, and he was hoping anything would come along. O’Brien said the Simpsons’ job saved his entire career because things could have turned out very differently.
Bad Luck on His First Day
On O’Brien’s first day in the office for The Simpsons, he was led to his office and began to work on show ideas. After a few minutes of working, he left his office to get coffee and suddenly heard a loud crash.
He came back to find a hole in his window and a dead bird on the floor. The other writers teased Conan and said it was a bad omen, which is not how you want to be labeled on the first day. Luckily, it turned out to just be a case of bad luck.
He Wasn’t the First Choice
When David Letterman left the Late Night franchise at NBC for his own show on CBS in 1993, O’Brien wasn’t the first choice for his replacement. The original replacement was going to be Dana Carvey. However, Carvey turned down NBC’s offer.
Carvey went on to host his own comedy show, The Dana Carvey Show, in 1996. Meanwhile, O’Brien first auditioned to be the new Late Night show host on the set of The Tonight Show with Jay Leno. O’Brien ended up getting the part over Jon Stewart, Drew Carey, and Paul Provenza.
Tough Critics
After the airing of his first Late Night episode, The New York Times Opinion section released a negative review of the show titled “O’Brien Flops!” Curiously enough, O’Brien was the one who wrote the article. No one understood why he would write that about himself.
O’Brien concluded, “As much as this writer would like to root for Mr. O’Brien, one can’t help but have grave doubts about his prospects.” In the article, O’Brien called himself arrogant and cocky. He was his own worst critic, but we don’t know how this was supposed to help his show.
He Had Cosmetic Surgery
It might be hard to believe, but O’Brien’s nose is not the one he was born with. It wasn’t because he chose to have a nose job but rather because he was attacked in high school. A youth street gang beat him up, and his nose was like a bag of bones, according to his doctor.
O’Brien was rushed to the emergency room, and he had to have corrective surgery to restore his nose. Unfortunately, the doctors had to work hard to fix it because it was so severely beaten.
A Strange Domain Name
In 2006, O’Brien said that one of the Late Night show’s band members was viewing a website called hornymanatee.com. In an effort to limit the company’s liability, NBC purchased the domain name for $159. However, they didn’t shut down the website.
Instead of closing the website, O’Brien’s writers extended the joke by transforming the domain into an actual website that was soon visited by over three million fans. Sometime around January 2010, the website was taken down. If you type in the domain, it redirects you to NBC’s homepage.
Scary Stalker
As a famous person, O’Brien has had his fair share of stalkers. However, one incident, in particular, scared him. In September 2006, O’Brien was stalked by a Roman Catholic priest named David Ajemain. He was upset because he was denied entry into the audience of a Late Night taping.
Ajemain sent O’Brien several threatening letters and once attempted to forcefully enter a Late Night taping. He was later arrested and eventually apologized in a New York Court. Ajemain and his family were ordered to stay away from O’Brien’s house and office for two years.
Paid to Leave
When O’Brien got the opportunity to host Late Night with Conan O’Brien, he was still under contract with The Simpsons. They were reluctant to let him leave and insisted that he fulfill the terms of the agreement or pay damages for breaking it. However, O’Brien couldn’t pass up the hosting opportunity.
Therefore, NBC agreed to pay half of the contract, and O’Brien decided to pay the other half to break the contract. It cost a total of $13,000. It’s a good thing the Late Night job worked out for him. He made more as a host than as a writer.
Late Night Meets The Office
Many of The Office cast members have a lot to thank O’Brien. John Krasinski, Ellie Kemper, and Mindy Kailing were all interns on Late Night with Conan O’Brien. They all have some adorable throwback photos from their time writing for the show.
They all looked so young and fresh-faced. O’Brien probably never guessed that they would go on to be part of one of the best sitcoms on TV and some of the biggest stars in Hollywood. These three weren’t the only ones whose careers O’Brien helped jumpstart.
His Late Night Sister
In the early years of Late Night with Conan O’Brien, a young Amy Poehler played the recurring character of Andy Richter’s “sister” Stacy. She was a dorky, brace-wearing girl who had a crush on O’Brien and would fly into a rage when her advances were rejected.
This helped Poehler get into the industry before she became an established household name. Other stars like Bob Odenkirk, Andy Richter, and a scandal-free Louis C.K. worked as writers for O’Brien’s show. He is still friends with many of these people.
His Friendship With Paul Rudd
If you have watched any of O’Brien’s shows, you might’ve noticed that Paul Rudd is a frequent guest. Rudd and O’Brien have a good friendship, and he is always a hilarious guest. Rudd has also successfully pranked O’Brien’s audience for the last fifteen years.
When Rudd comes on the show to promote his latest movie, he always promises to show an exclusive clip from it. However, instead, he shows a scene from the 1988 alien movie Mac and Me, which depicts a child in a wheelchair falling from a cliff.
Fake Feud
In 2008, there was a Writers Strike, so O’Brien decided to liven things up by staging a fake feud with Stephen Colbert and Jon Stewart. The so-called feud was based on which of the three hosts gave the Republican presidential campaign a slight bump in the polls.
The feud ended in an “all-out-brawl” between O’Brien, Colbert, and Stewart. The hilarious skit was caught on camera, and Colbert even tried to pull out a gun. Viewers loved the feud because it provided a distraction from the Writers’ Strike issue.
On-Air Concussion
Throughout the years of his talk show, O’Brien has done a lot of crazy things. However, one of his stints went a little too far when Terri Hatcher of Desperate Housewives appeared as a guest on The Tonight Show.
The two were doing a skit in wetsuits when O’Brien slipped on the soundstage and hit his head on the floor. He remained professional and managed to slur his way through the rest of the sketch. Eventually, the show cut to a commercial, and O’Brien had to go to the hospital.
Let’s Be Friends
In the early 1990s, O’Brien briefly dated Lisa Kudrow, who was starting to gain fame for her role on Friends as Phoebe. Kudrow convinced O’Brien that he should begin performing comedy as well as writing. O’Brien was happy with his job and disagreed with Kudrow.
They met in an improv class early on in Kudrow’s career and have remained close friends over the years. Kudrow was one of the only people in O’Brien’s life who said he had to go for it when he talked about the Late Night opportunity.
He Pranked Bill Cosby
When O’Brien was 19, he pulled the ultimate prank on Bill Cosby. During his time at Harvard, O’Brien wanted to meet one of his comedy idols and hatched a devious plan to do so. He contacted Cosby, claiming that he was being awarded a lifetime achievement award from Harvard.
O’Brien said that Cosby needed to fly to the school to accept it, and Cosby took the bait. He arrived at Harvard in his private plane, and O’Brien picked him up in his parents’ station wagon. O’Brien presented him with an old bowling trophy.
College Clown
When O’Brien was the editor of The Harvard Lampoon, he was arrested after stealing an entire shipment of the Harvard newspaper. Coincidentally, the editor of the newspaper at the time was Jeff Zucker, who later became an NBC executive and would help O’Brien’s career.
Later on, it was Zucker who decided to replace O’Brien with Jay Leno on the Tonight Show. Maybe Zucker wanted to get revenge for the newspaper prank. Although he removed O’Brien from the show, it didn’t hurt his career, and he went on to have his own show.
He Diffused Tension in The Simpsons Writing Room
During his few years working as a writer for The Simpsons, O’Brien built up quite a reputation in the writer’s room. He helped create some of the most iconic episodes, was as well as being a fun person to work with, according to the other writers.
When tensions got high, O’Brien had a hilarious way to diffuse any tension when people pitched ideas. He used to have a running joke where he would open a can of Diet Coke, then nervously pitch a joke to the rest of the room. He always made sure the can would spray all over him.
O’Brien and Robin
If there is one thing he should be known for besides his talk show, it is his pranking skills. O’Brien is a pranking mastermind. He stole Robin’s (Batman and Robin) tights in the 1980s. Burt Ward, who played Robin on the Batman TV series, spoke at Harvard and brought his famous costume.
During Ward’s speech, O’Brien and his friends dressed up as security guards and stole the costume. The group then prank-called Ward pretending to be various Batman villains before giving the suit back.
He Cares About His Crew Members
Even though he is the ultimate prankster, O’Brien is one of the most admirable men in show business. He is known for treating his employees well and has given them money out of his pocket. In 2010, during the Tonight Show conflict, NBC tried to screw O’Brien out of his job.
O’Brien refused to comply with NBC’s demands to switch back to the original 12:05 slot. This meant that contract negotiations had to begin for O’Brien to leave the network. He was given a buy-out of $45 million, while his staff got $12 million. O’Brien ended up paying money to the 50 stagehands who weren’t included in the payout for six weeks of severance.
He Wrote the 4th Most Popular Simpsons Episode
Many fans of The Simpsons might not realize that O’Brien wrote some of the show’s most iconic episodes. The infamous monorail episode featured Marge trying to battle the construction of an invasive monorail system in the middle of Springfield.
The monorail episode also happens to be O’Brien’s favorite episode of the show, and we can understand why. The hilarious song that the upbeat salesman sings in the town hall is memorable. The episode boasts the highest throwaway-gag-per-minute ratio of any episode. That’s something to be proud of.
Tom Hanks Gave Him a Special Nickname
Throughout the years, O’Brien has had some very big names on his show. He has been lucky enough to have Tom Hanks as a guest multiple times. However, things haven’t always gone right when Hanks has been a guest.
During one episode, Hanks referred to O’Brien as “Coco,” and the name stuck. Apparently, O’Brien hates that the rest of America has gone along with this special nickname. Luckily, O’Brien doesn’t take it too seriously. He also used the name for his website. HH
He Was the Oldest Person to Be Named as The Tonight Show’s New Host
Before the controversy began with his role as The Tonight Show’s host, O’Brien was the oldest person ever to be named the show’s host. He was 46 when NBC made their announcement. He also made the record for the shortest-serving host of the series in NBC history.
O’Brien is now on TBS and hosts his own show titled Conan, which has allowed him to return to his late-night roots. While he was briefly in the top spot at NBC, his first guest on the show was Will Ferrell, and Pearl Jam was the first-ever musical act.
Ordained Host
Unless you are an avid watcher of O’Brien’s show, you probably wouldn’t know that he is an ordained minister and performed a same-sex marriage that was broadcast on his show. He specifically got ordained to perform this wedding.
A member of his staff and his partner wanted to get married, so O’Brien got ordained to perform their wedding during the taping of his show. He really cares about his staff, and the couple was excited to share their wedding with O’Brien and his audience.
Chance Encounter
O’Brien and his wife, Liza Powel, have been married since 2002, and the way they met is adorable. In 2000, O’Brien was filming a skit at an advertising agency called Foote, Cone, and Belding. Powel was a young copywriter at the time, and she met O’Brien.
The couple hit it off while they were taping the skit and dated for 18 months before getting married. Now they have been married for almost 20 years, and they have two children together. They really are the ultimate couple goals.
The Prank Master Strikes Again
O’Brien was always pulling pranks in college, and it’s shocking he made it through his four years. Once while he was at school, he pranked both the local and state police at the same time. He and his friends rented a jackhammer and dressed as construction workers.
O’Brien then called the Boston police and told them that college students were illicitly dressed as construction workers and were jackhammering the street. He then called the state police and said college students were dressed as police officers harassing construction workers so that the state police would arrest the local police.
And the Award Goes To…
Throughout his time in the industry, the Emmys have been both kind and unkind to O’Brien. Between 1997 until 2013, he was nominated for at least one Emmy each year, but he only won twice. In 2007, he was awarded Outstanding Writing for a Comedy, Music, or Variety Series.
His second award was in 2012 for Outstanding Achievement in Interactive Media for his show Conan. Well, you know what they say: It’s just an honor to be nominated, right? Maybe one year, he will sweep all the categories he is nominated in.
Karaoke King
In 2010, O’Brien went on a 30-city live tour called Legally Prohibited From Being Funny. As the news broke about his TBS show, he was touring, so it was the perfect way to promote his upcoming program.
During the shows, he showed off his music skills by playing guitar and singing for the audience. O’Brien performed many covers of songs, including Radiohead’s “Creep” and Gloria Gaynor’s “I Will Survive.” He is definitely someone we would go to karaoke with because he knows how to rock out.
What Could Have Been
Before his career took off and he landed his writing role for The Simpsons, O’Brien and fellow writer Robert Smigel wrote a TV pilot starring Adam West. The pilot was called Lookwell and centered around West, who played the character Ty Lookwell.
The character of Ty Lookwell was supposed to be an older, washed-up former action hero who is deputized in a small town and attempts to solve real crimes. However, the show was never picked up by the network, but the pilot episode is now celebrated as a cult classic.
He Only Follows One Person on Twitter
O’Brien is very selective about whom he follows on social media. On Twitter, he only follows one person, and that person was chosen at random in 2010. He once tweeted, “I’ve decided to follow someone at random. She likes peanut butter and gummy dinosaurs. Sarah Killen, your life is about to change.”
Sarah Killen only had three followers at the time, but because of O’Brien, her following grew to over 400k. She is one fortunate girl, and Killen should return the favor by only following O’Brien, so it is an exclusive Twitter relationship.
Playing Hard to Get
One person O’Brien always tried to get on his show was Hunter S. Thompson. He kept asking the author to be a guest, but Thompson turned down many invitations until he finally agreed, under one condition. He was not going to make it easy for O’Brien.
Thompson requested that O’Brien and his crew fly to his farm in upstate New York and shoot the segment remotely from the farm while shooting guns and drinking hard liquor. O’Brien agreed and filmed the segment while boozed up and shot the NBC peacock with a machine gun.
Down in Havana
In 2015, O’Brien took the crew of his show to Cuba to tape a series of remote segments. This was a groundbreaking series of segments because it was the first time a late-night television host taped a show in Cuba since Jack Paar taped The Jack Paar Tonight Show in Cuba in 1959.
There is a lot of censorship and poor internet there, but they managed to show off the vibrant culture of Cuba. He explored Havana, went to famous restaurants, and drove around in classic cars through the colorful streets of Havana.
Week-to-Week Contract
When Conan took over for David Letterman on Late Night, he initially had a week-to-week contract because NBC had zero confidence in his capabilities. Meanwhile, they were looking for a replacement because they were sure he was going to fail miserably, but they were wrong.
Of course, we now know that they eventually realized he was fit for the job because O’Brien was the show’s host for 14 seasons. He did many great things throughout his time as the host, but his relationship with NBC didn’t end well even though he proved himself.
Dancing Dreams
O’Brien is a man of many talents, and as a young child, he dreamed of becoming a professional tap dancer. When he was young, he thought every great entertainer needed to be an excellent singer and dancer. O’Brien wanted to be in show business but didn’t grasp how to do that when he was eight.
He begged his parents for tap lessons, and they couldn’t say no. O’Brien confessed to Rolling Stone, “I had these antiquated ideas of what an entertainer was. You don’t have to know how to tap-dance. Tony Danza thinks you do, but you don’t have to know how to be a tap-dancer today.”
Greg Kinnear Nearly Took His Job
When O’Brien was struggling on Late Night, other stars started biting at his heels to take his hosting spot. One of the contenders for the job was Greg Kinnear. Apparently, NBC executives were revisiting his position on a weekly basis.
If things had fallen through with O’Brien, Kinnear would have gotten the position. He was already hosting Later, the show after Late Night, and he became NBC’s number one choice to replace O’Brien, but that never happened. Despite the critics, O’Brien persevered and even had Kinnear as a guest on the show.
He Would Sneak Into Letterman’s Studio
By now, we all know about O’Brien’s mischievous ways. However, out of all his pranks, this one takes the cake because he had an old habit of sneaking into Letterman’s Late Night studio and using the desk to write material. He hoped it would give him inspiration.
O’Brien said the point of that story is that NBC has terrible security, and he was sure that every night there would be a weird person sitting at his desk when he got the Late Night job. We are sure NBC upped their security systems after O’Brien shared this story.
Beef With Jay Leno
After O’Brien took over the Tonight Show in 2009, it was as if he finally reached the peak of his career. However, it wasn’t long before Jay Leno pushed him out of the spot. The drama that followed was referred to as the Late Night Wars.
For the next few months, every late-night host at the time (Letterman, Jimmy Kimmel, and Craig Ferguson) took jabs at Leno. When Leno finally gave up The Tonight Show spot to O’Brien, he got a show that aired 30 minutes before O’Brien’s. NBC eventually moved him back to his time slot, and O’Brien left The Tonight Show.
He Performed on Stage as a Child
As a child, O’Brien wanted to be an entertainer when he grew up. In a 2011 interview, he revealed that he put on plays as a kid, much like other young performers. O’Brien even performed some of the plays at his school, but they didn’t always go as planned.
O’Brien always insisted his show be like what he thought real show business would be like, with a 25-minute intermission seven minutes into a 15-minute show. He just wanted his performances to be authentic, but it turned out to be a fiasco.
He Loved Writing for Mr. Burns
When people think about their favorite Simpsons characters, they probably think about Bart, Homer, or Lisa. However, O’Brien’s favorite character was Mr. Burns. He’s the last character that comes to mind, but O’Brien saw him as comedy gold, and he loved writing him into episodes.
In an interview with Vanity Fair, O’Brien explained that he loved Mr. Burns because he possesses three perfect qualities for comedy writing. According to O’Brien, Mr. Burns was old, rich, and evil, making him a character with limitless comedic potential.
He Went to Court for Joke Theft
While we all know O’Brien is hilarious, he had a bit of trouble with his jokes in 2015. Comedy writer Alex Kaseberg noticed some of the jokes he wrote on his blog and Twitter appeared in O’Brien’s monologues, so he sued the Late Night host.
At the time, a Southern California District of California judge dismissed the claims for two of the jokes, but O’Brien had to go to court for the other three jokes. When the suit was presented, O’Brien’s reps said they were confident he would be vindicated. They ended up settling a deal.
Losing The Tonight Show Wrecked Him
Although many people see O’Brien smiling and laughing on TV, there was a time in his life when he was depressed. After losing The Tonight Show job, he put on a brave face, but he was a mess inside. He went on tour with his band but realized he had to face reality eventually.
O’Brien felt like he had been in a car accident. He returned home after the tour with a mix of emotions. His wife remembers that he would just walk from room to room, not leaving the house. Today he has his own show with much more freedom, and his empire has grown exponentially since he left NBC.