It’s safe to say that Conan O’Brien has had an illustrious career in television. He started off as a writer on programmes such as Saturday Night Live before being chosen as the new host of Late Night in 1993. Like most US talk show hosts, people were initially unimpressed with his performance, but after a few bumps in the road O’Brien has become one of America’s best-loved (and longest-serving) presenters.

He’s also hosted prestigious events such as the Emmy Awards and has made guest appearances on comedy classics such as The Office and 30 Rock. But despite enjoying such a long career in the limelight, there are still plenty of things that we don’t know about Conan O’Brien.

In the article below, we’ve brought you 21 fascinating bits of trivia about O’Brien that you probably didn’t know before. We reveal the startling event that occurred during his first day working on The Simpsons, plus you can find out the traumatic reason why he had to get facial plastic surgery in high school.

21. The Simpsons saved O’Brien’s career

Did you know that Conan O’Brien used to be a writer on The Simpsons?

[adunit mobile=”RTK_dVa8″]

Not only that, the show host credits the animated series with saving his entire professional career! O’Brien quit his job with Saturday Night Live in 1991 with no other work lined up and nothing else to do. Understandably he was a little bit worried…

O’Brien later reflected on that period of time: “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.”

[adunit mobile=”RTK_wCZW”]

Funnily enough, this basically happened when The Simpsons called O’Brien up and offered him a writing job! As a result, the show host has claimed that the animated series saved his entire career. Things could have been very different…

Unfortunately disaster struck on O’Brien’s very first day in the office. He was working on some ideas when a bird crashed through one of the office windows and promptly passed away from the impact.

[adunit mobile=”RTK_z9hm”]

The other writers teased Conan and said it was a bad omen! Luckily it turned out to be anything but, when he was eventually selected to present a late night talk show while still working at The Simpsons.

20. He only follows one person on Twitter

Conan O’Brien is pretty active on social media.

[adunit mobile=”RTK_dVa8″]

Like most good chat show hosts, he has his own Twitter account, but have you ever noticed anything strange about his profile? If you look carefully, you can see that O’Brien only follows one fellow Twitter user. There’s kind of a weird story behind the one follower thing too…

Shortly after joining the site in 2010, O’Brien decided that he was only going to follow one random fan, and the lucky person to be selected for this honour was a lady named Sarah Killen.

[adunit mobile=”RTK_wCZW”]

Killen had just started following O’Brien when he noticed that she only had three other followers, so he decided to help her out! Of course, he let everybody know on social media too:

Thanks to O’Brien’s tweet, Killen now has over 400,000 followers. Not bad!

[adunit mobile=”RTK_z9hm”]

We’re sure Conan is pleased with that one too:

19. He had to have cosmetic surgery after being attacked in high school

Conan O’Brien has some very distinctive features, but he’s also gone under the knife. Conan O’Brien’s plastic surgery happened after he was attacked while still at school. The plastic surgery was mostly required to reconstruct his nose after severe injury.

[adunit mobile=”RTK_dVa8″]

But it turns out that in the past he’s been forced to undergo cosmetic surgery. In particular, Conan’s nose is not the one that he was born with, thanks to a horrible incident that occurred when the future talk show host was still in high school.

O’Brien once revealed what happened during an interview with Marc Maron on the WTF podcast. O’Brien explained that he was viciously attacked by a youth street gang when he was still a high school student.

[adunit mobile=”RTK_wCZW”]

The poor guy was rushed to the emergency room after being beaten to a pulp by the gang. And things really weren’t looking good for Conan’s poor nose.

Clearly able to feel the pain, O’Brien nervously asked the doctor if his nose was broken. The doctor replied: “Broken? Good god, man, it’s a bag of bones!” Yikes!

[adunit mobile=”RTK_z9hm”]

Corrective surgery swiftly followed to try and restore O’Brien’s nose to its original state.

18. He owns a website called

Yes you did read that correctly!

[adunit mobile=”RTK_dVa8″]

It’s not very safe for work, but there is an actual website called – and it’s all thanks to a skit on O’Brien’s Late Night show. So why is O’Brien responsible for this bizarre URL?!

In 2006, Late Night suggested that one of the show’s band members was absent because he was too busy looking at a website called NBC wanted to make sure that they didn’t get sued by anyone and snapped up the rights to the website.

[adunit mobile=”RTK_wCZW”]

Apparently the domain name only cost $159, which helped to limit the company’s liability. But Conan and his writers didn’t stop at simply buying the rights to the website.

They decided to transform the URL into a proper website and included plenty of disturbing photographs of the manatee in question. It was soon visited by over 3 million Conan fans around the world.

[adunit mobile=”RTK_z9hm”]

Just make sure you don’t access the site on a work computer…

17. He was once stalked by a priest

It’s safe to say that Conan O’Brien is a hugely recognisable public figure.

[adunit mobile=”RTK_dVa8″]

But with that fame comes a lot of extra hassle. In fact, from September 2006 onwards, O’Brien was the victim of a stalking campaign by a former Roman Catholic priest named David Ajemian.

Ajemian began his harassment after being refused entry to the audience of a Late Night taping. He then pursued the show host and sent a series of threatening letters to Conan’s office.

[adunit mobile=”RTK_wCZW”]

He was eventually arrested after forcibly trying to enter another Late Night taping and was ordered to attend a mental health facility for his behaviour.

Funnily enough, O’Brien himself is actually an ordained minister! He once performed a same-sex marriage during a taping of his show for one of his staff members.

[adunit mobile=”RTK_z9hm”]

Wow! Imagine having your marriage officiated by Conan O’Brien…

16. Most of his interns went on to star in The Office US

The Office US cast have a lot to thank Conan O’Brien for.

[adunit mobile=”RTK_dVa8″]

In a very strange twist, no fewer than three main cast members of the popular sitcom all used to work as interns on Late Night With Conan O’Brien. And they all have some very cute photographs commemorating their time writing for the show. Check it out:

John Krasinski, Ellie Kemper and Mindy Kaling were all interns on Late Night before eventually joining The Office US. Don’t they look fresh-faced?!

[adunit mobile=”RTK_wCZW”]

And The Office isn’t the only series that has Conan to thank for nurturing young talent. He’s also responsible for kick starting the career of Amy Poehler.

When Late Night first started airing, one of the recurring characters to appear was Andy Richter’s crazy sister Stacy. She wore braces and had a hilarious crush on O’Brien, which often drove her to some strange behaviour.

[adunit mobile=”RTK_z9hm”]

Stacy was played by a young Amy Poehler.

15. He graduated magna cum laude from Harvard

Conan has definitely got a lot of intelligence to go alongside his charisma and success.

[adunit mobile=”RTK_dVa8″]

It’s one of the aspects of his personality that have really helped to shape his comedy and appeal. O’Brien’s academic success started very young when he was selected to be his high school’s valedictorian. He was also the managing editor of his high school newspaper.

Afterwards, O’Brien joined the Ivy League and went on to earn himself a spot at Harvard, where he ended up graduating magna cum laude. His major was in history and literature.

[adunit mobile=”RTK_wCZW”]

Since then, the talk show host has visited his alma mater several times and has participated in talks at his old college.

The reason for his brains might have something to do with O’Brien’s parents. His father is a professor of medicine at Harvard Medical School, while his mother is a lawyer and partner at a law firm in Boston.

[adunit mobile=”RTK_z9hm”]

Not a bad start in life for O’Brien!

15. He staged a fake feud with Jon Stewart and Stephen Colber

The press are always trying to stoke up feuds between the talk show hosts.

[adunit mobile=”RTK_dVa8″]

So during the Writers Strike of 2008, Conan decided to take matters into his own hands and stirred up a fake feud with his ‘rival’ hosts Stephen Colbert of The Colbert Report and Jon Stewart of The Daily Show.

Viewers ended up loving the feud and it provided a welcome distraction from the Writers Strike issue. Basically the ‘problem’ started when the three presenters were trying to decide who was responsible for Mike Huckabee’s waning popularity.

[adunit mobile=”RTK_wCZW”]

At the time, Huckabee’s Republican presidential campaign was hitting a few bumps in the polls, so the three got together to try and work out what was going wrong.

A hilarious skit was caught on camera which eventually ended in an “all-out-brawl” between O’Brien, Colbert and Stewart.

[adunit mobile=”RTK_z9hm”]

Colbert even tried to pull out a gun!

14. He once suffered a concussion live on air

O’Brien has done a lot of crazy things on his show over the years.

[adunit mobile=”RTK_dVa8″]

But things didn’t go quite to plan when Teri Hatcher of Desperate Housewives fame appeared as a guest on the Tonight Show. In fact, O’Brien ended up having to go to hospital!

The pair were in the middle of a skit and were both wearing some rather fetching wet suits when the accident occurred.

[adunit mobile=”RTK_wCZW”]

O’Brien slipped on the soundstage and hit his head on the floor. Hard. Somehow the presenter remained a professional and managed to slur his way through the rest of the dialogue.

Eventually the show cut to a commercial and O’Brien had to be treated in hospital. Talk about dedication!

[adunit mobile=”RTK_z9hm”]

At least he managed to finish his monologue in time.

13. He pulled an epic college prank on Bill Cosby

Bill Cosby isn’t exactly making headlines for the right reasons at the moment.

[adunit mobile=”RTK_dVa8″]

But back in the day, when O’Brien was at college, Cosby was one of the most popular actors on US television. And what did O’Brien decide to do about that? Pull a prank on Cosby, of course!

At the tender age of 19 years old, O’Brien was a Harvard student and wanted to pull an elaborate prank on his comedy idol. He contacted Cosby and claimed that the comedian was going to be given a lifetime achievement award.

[adunit mobile=”RTK_wCZW”]

He also said that Cosby would have to fly to the school and accept it. Amazingly, Cosby took the bait and showed up to Harvard thinking he was about receive a prestigious award.

Cosby took a private jet to the university campus before being picked up in O’Brien’s parent’s station wagon and escorted to the ceremony…where he was awarded an old bowling trophy!

[adunit mobile=”RTK_z9hm”]

Thankfully Cosby saw the funny side!

12. He had a genius way of diffusing tension in the Simpsons writing room

O’Brien was at The Simpsons for a few years, and he built up quite a reputation during his tenure on the show.

[adunit mobile=”RTK_dVa8″]

He helped to create some of the most iconic episodes on the series (more about that below), but we bet he was a lot of fun to work with behind the scenes too. Why?

Apparently Conan developed a hilarious way of diffusing any tension in the writers room whenever people were pitching ideas.

[adunit mobile=”RTK_wCZW”]

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 writers.

No matter how the joke was received, Conan would always fizz up the can of Coke and proceed to spray it all over himself, giving everyone else in the room a good laugh in the process!

[adunit mobile=”RTK_z9hm”]

We’re sure that helped to take the awkwardness out of any writers meetings. Nice one Conan!

11. He once stole Burt Ward’s Robin costume

We’ve already seen that Conan used to be quite the prankster.

[adunit mobile=”RTK_dVa8″]

As well as winding up Bill Cosby during his time at Harvard, the future talk show host once stole Burt Ward’s infamous Robin costume from his days on the popular Batman TV series in the 1960s.

The elaborate prank was devised while Conan was editing The Harvard Lampoon and decided to ask Ward to come and speak at the college campus.

[adunit mobile=”RTK_wCZW”]

Ward decided to bring along his costume to get the crowd going, but didn’t put it on and instead left the outfit with a security guard while he was speaking.

In the middle of Ward’s speech, the lights suddenly went out and a man dressed in a penguin costume asked “When is a security guard, not a security guard?”. The fake security guards then stole the costume and ran away!

[adunit mobile=”RTK_z9hm”]

For the next few hours, Conan and his accomplices prank called Ward and pretended to be different Batman villains. Luckily for Conan, Ward has a very good sense of humour and the outfit was eventually returned.

10. He had to pay to leave The Simpsons

O’Brien was one of the top writers on The Simpsons.

[adunit mobile=”RTK_dVa8″]

So when he was lured away by the exciting prospect of The Late Night Show, executives at Fox wanted to try and get him to stay. When Conan was offered the top job, he still had over a year left on his Simpsons contract.

This created a slightly awkward situation when it came to Conan trying to follow his dreams! However, NBC agreed to pay half of Conan’s yearly salary, if Conan could pay for the other half.

[adunit mobile=”RTK_wCZW”]

This deal released him from having to carry out the rest of his work on the animated series – but how much did it cost the talk show host?

Apparently he had to fork out $130,000 of his own money to get out of the contract. Wow!

[adunit mobile=”RTK_z9hm”]

It’s a good job the whole hosting gig worked out in the end…

9. Conan personally paid the severance packages for 50 crew members working on The Tonight Show

Conan is known as one of the nicest guys in show business.

[adunit mobile=”RTK_dVa8″]

And is it any wonder why, when he treats his employees like this? During the infamous 2010 Tonight Show conflict, which saw NBC trying to screw O’Brien out of his much-deserved spot at the head of the programming, things got very heated.

During one of the most controversial moments in NBC history, O’Brien refused to comply with their demands for him to switch back to his original 12:05 slot. This meant that contract negotiations had to begin in order for O’Brien to leave the network.

[adunit mobile=”RTK_wCZW”]

Conan wanted to make sure that all of his employees who would be losing their jobs were looked after appropriately. Conan himself was given a buy-out of $45 million, while his staff received $12 million.

However, the severance package didn’t include 50 stagehands and other crew members. So to help out his former crew, Conan paid out severance to them for 6 weeks after he left NBC.

[adunit mobile=”RTK_z9hm”]

He really is one of the good guys!

8. He wrote the 4th most popular Simpsons episode of all time

Fans of The Simpsons might not realise that one of America’s most recognisable talk show hosts actually created some classic episodes of the animated series.

[adunit mobile=”RTK_dVa8″]

And far and away near the top of the list is the infamous Monorail episode, which featured Marge trying to battle the construction of an invasive monorail system in the middle of Springfield.

The Monorail episode also happens to be Conan’s favourite episode of the show and we can definitely see why! Remember the hilarious song that the super upbeat salesman sings to the town hall?

[adunit mobile=”RTK_wCZW”]

Not only that, but legendary Star Trek actor Leonard Nimoy also makes an appearance in the episode. In 2003, Entertainment Weekly ranked this episode as the 4th greatest in the show’s history.

Apparently it also boasts the highest throwaway-gag-per-minute ratio of any other episode.

[adunit mobile=”RTK_z9hm”]

That’s a pretty impressive episode to be responsible for coming up with!

7. He was the oldest person to be named as The Tonight Show‘s new host

Before the whole controversy began, there’s an interesting Tonight Show fact you might not know about…

[adunit mobile=”RTK_dVa8″]

Conan O’Brien was actually the oldest ever person to be named as The Tonight Show‘s new host – he was 46 years old when NBC made their announcement.

Of course, he also made a new record after being the shortest-serving host of the series when NBC decided to shake things up without really giving Conan a chance.

[adunit mobile=”RTK_wCZW”]

Conan is now on TBS and hosts his own eponymous show entitled Conan, which has really allowed him to return to his late-night roots.

While he was briefly in the top spot at NBC, his first guest was comedy legend Will Ferrell, while Pearl Jam was the first ever musical act.

[adunit mobile=”RTK_z9hm”]

It’s just a shame he wasn’t given more time to shine…

6. Tom Hanks gave Conan a very special nickname

Conan has had some very big names on his shows over the years.

[adunit mobile=”RTK_dVa8″]

And a couple of times he’s been lucky enough to have Mr Tom Hanks in the guest chair. But things haven’t always gone right when Hanks has been on the show…

In fact, during one episode, Hanks randomly started referring to Conan as ‘Coco’…and the name stuck!

[adunit mobile=”RTK_wCZW”]

Apparently O’Brien hates it, but the rest of America seemed to go along with Hanks’ special nickname.

Luckily Conan didn’t take it too badly and since then, Hanks has appeared on Conan’s shows several more times.

[adunit mobile=”RTK_z9hm”]

Here they are enjoying a nice bit of scotch together:

5. Plenty of stars have worked for Conan in the past

We’ve already mentioned some of the famous interns who used to work on Conan’s show…

[adunit mobile=”RTK_dVa8″]

But the cast of The Office US aren’t the only people to have worked for the ginger-haired talk show host. If you’re a fan of Breaking Bad and Better Call Saul then you’ll definitely recognise this face:

That’s a very young Bob Odenkirk in the writing rooms for Conan’s Late Night series. He would later go on to have a hugely successful TV career of his own with the role of Saul Goodman in Breaking Bad and its spin-off.

[adunit mobile=”RTK_wCZW”]

Odenkirk isn’t the only famous name to have worked as a writer on the show either. Do you recognise some of these faces?

Andy Richter is hiding behind the mask, while Louis C.K. is front and centre, looking very fresh-faced (and scandal free at that time).

[adunit mobile=”RTK_z9hm”]

Looks like working for Conan is a pretty sweet gig!

4. David Letterman saved Conan’s spot on The Late Night Show

Conan once came out with a very emotional tribute to none other than David Letterman.

[adunit mobile=”RTK_dVa8″]

O’Brien took over the The Late Night Show and like every other host in TV history, it took a while for ratings to get going. But for a good while, NBC had no patience with O’Brien and came very close to firing him.

In 1994, O’Brien used his opening monologue to explain how Letterman’s guest appearance on his show had helped to save O’Brien’s entire hosting career.

[adunit mobile=”RTK_wCZW”]

He admitted that things had been going wrong and that “the network started to make it clear that [he] probably wouldn’t be around for very long.”

A few months in, Letterman requested to appear on Late Night as a guest and after that, things went a whole lot better for O’Brien, who said: “At one of the lowest points of my life, when I was a 30-year-old national punch line, Dave – for reasons I still don’t really understand – completely rescued me.”

[adunit mobile=”RTK_z9hm”]

Thus Conan believes that he has a lot to thank his comedy idol for.

3. He really wanted to be a tap dancer

Conan is a man of many talents.

[adunit mobile=”RTK_dVa8″]

But did you know that as a young child he dreamed of becoming a professional tap dancer?! It seems that a young O’Brien thought that every entertainer needed to be excellent at singing and dancing…

He already knew that he wanted to be in show business, but didn’t quite grasp how to do that at the age of eight years old. So he begged his parents to enroll him in tap-dancing lessons!

[adunit mobile=”RTK_wCZW”]

O’Brien once confessed to Rolling Stone: “I had these very 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.”

“I used to go to these lessons. Just a group of young black kids and this skinny white kid with bright orange hair and his tap shoes in a box.”

[adunit mobile=”RTK_z9hm”]

Just thinking about what he must have looked like back then is pretty hilarious!

2. Greg Kinnear nearly took Conan’s job on Late Night

Back when Conan was struggling on Late Night, other people were starting to bite at his heels.

[adunit mobile=”RTK_dVa8″]

And one of these contenders for the job was none other than…Greg Kinnear?! Apparently NBC executives were revisiting Conan’s position on a weekly basis.

And if things fell through, their back-up plan was to replace Conan with Kinnear. We’re not really sure how that would have worked out, but it’s nice to know they had a ridiculous plan to fall back on.

[adunit mobile=”RTK_wCZW”]

Apparently Kinnear was already hosting Later, the show that followed Late Night, and he became NBC’s number one choice to replace Conan if it came to sacking him. Luckily Conan’s viewing figures picked up before that had to happen.

However, one of O’Brien’s producers confessed that they were very near to being sacked: “I’m afraid to say we probably don’t know how close we were to getting canceled. Part of me has a morbid curiosity. I think we got a lot closer than we think.”

[adunit mobile=”RTK_z9hm”]

Despite the critics being united against O’Brien, he eventually won out!

1. He used to sneak into Letterman’s studio to write material

OK, so by now we know all about Conan’s mischievous ways.

[adunit mobile=”RTK_dVa8″]

But the one that really takes the cake is his old habit of sneaking into Letterman’s Late Night studio and using the desk to write material!

Apparently he would sneak into the studio after working on SNL in the 80s and early 90s, to try and get some inspiration for his writing.

[adunit mobile=”RTK_wCZW”]

Wow! That’s a nice bit of comedy trivia right there. O’Brien himself said: “Really, the point of the story is that NBC has terrible security, and I’m sure now every night there will be a different weird person sitting at my desk.”

Did you know all of these facts about Conan O’Brien? Let us know in the comments section!

[adunit mobile=”RTK_z9hm”]