The Double Life Of Conan O'Brien

He's been around for decades, and from his time at Saturday Night Live and The Simpsons to his turbulent reign as one of the kings of late-night television, Conan O'Brien has always been comedy of the light-hearted, goofy variety. Never appearing to take himself too seriously and always the first to make jokes at his own expense, the world has come to recognize O'Brien as the good-hearted, light comedy fare that's most funny in the hours when one day is slowly creeping toward the next. But he hasn't always been the self-assured comedian we recognize today. In fact, he's he's had some incredibly dark times in his life.

He was incredibly intimidated when he started on The Simpsons

Conan O'Brien is so completely associated with his late-night television show career that it's easy to forget that he got his foot in the door in a completely different arena: writing for The Simpsons. He talked to Vanity Fair about his experiences working behind-the-scenes on one of the most famous cartoons in the world, during which he revealed he absolutely wasn't the self-assured, stand-up comic we see today. Not only was he incredibly intimidated to work alongside some of the writers and comics he'd grown up idolizing, his first day was tainted by an event that he took as a very, very dark omen.

"I was very nervous," he told the magazine. "I knew a bunch of the writers, but just by reputation—I hadn't worked with many of them. I was self-conscious, I was worried: 'Can I do it? Am I going to embarrass myself in front of all these people?'"

Things took a turn for the weird when they showed him his office. "[They] told me to start writing down some ideas," he recalled. "They left me alone in that office, and I remember leaving after five minutes to go get a cup of coffee. And I heard a crash, and I walked back to the office, and there was a hole in the window and a dead bird on the floor—literally in my first 10 minutes at The Simpsons, a bird had flown through the glass of my window, hit the far wall, broken its neck, and fallen dead on the floor. And I remember George Meyer came in and looked at it, and he was like, "Man, this is some kind of weird omen."

He's not shy about calling out his own writers

O'Brien's self-deprecating sense of humor goes a long way into painting him as one of the most down-to-earth, modest of the group of late-night talk show hosts, but he's not afraid to stand up to anyone who takes aim at his show—especially when it's one of his own.

In 2015, writer Andres du Bouchet took to Twitter in an incredibly ill-thought move, tweeting his thoughts about the state of late-night comedy. His tweets weren't flattering, like the one in which he declared that "Comedy in 2015 needs a severe motherf***king shakeup. No celebrities, no parodies, no pranks, no mash-ups or hashtag wars. I'm fat."

He went on to compare the current state of late-night comedy to high school humor, and the irony of some of the cursing and less-than-mature observations he made about the industry seemed to slip by his own comedic radar.

Du Bouchet's tweets didn't slip by O'Brien's radar, however. In fact, amid the controversy, the affable host chimed in and called him out in a brief, yet hilarious tweet. "I wish one of my writers would focus on making my show funnier instead of tweeting stupid things about the state of late night comedy," he wrote. Burn.

He's suffered from depression and anxiety

He may be one of the funniest men on television, but behind the scenes, O'Brien's life hasn't always been filled with sunshine and happiness. In fact, speaking to radio host Howard Stern in 2015, the late-night host opened up about his years-long battle with depression and anxiety, and the medication he finally took to help treat it.

"To come here to do the show, we just walked near 30 Rock, which is where I did the NBC show for ... 16 years ... and also Saturday Night Live for almost, what, three, four years? So, almost 20 years in that building. And I loved it; it was great ... But I remembered, just walking here ... walking near 30 Rock and remembering every morning walking into that building and having this incredible anxiety. You feel like it's a low-ceiling cloud ... I would take the elevator up, and my heart's pounding, [thinking], 'We've got to make [the show] good.' [There was a lot of] pressure."

He once got handcuffed by police

Most people assume that O'Brien's feud with former NBC exec Jeff Zucker was the result of the fallout from his embarrassing and high-profile exit from The Tonight Show in 2010; but as it turns out, it all dates back to their college days at Harvard.

At the time, Zucker ran the straight-shooting Harvard Crimson; O'Brien, meanwhile, led the Crimson's humorous rival, the Harvard Lampoon. Pranks were part of the rivalry, of course, although things got particularly out of hand when O'Brien engineered the theft of all issues of the Crimson a day before they were supposed to hit the streets. Zucker's response: to call the cops.

"My first meeting with Jeff Zucker was in handcuffs, with a Cambridge police officer reading me my rights," O'Brien told BusinessWeek (via The Wrap) in 2004.

"College pranks are supposed to be clever, but our rivalry with the Crimson had degenerated into us stealing something, Jeff calling the police, and the police making us haul it back," O'Brien previously mentioned in a 2001 interview with the New Yorker.

For what it's worth: the two appeared to shake hands and make up at a 2015 television event, according to the Hollywood Reporter. Still, given their long history together, we doubt they'll be calling each other to grab drinks anytime soon.

Not all his college pranks were harmless fun

According to Harvard Magazine, O'Brien once pulled off a prank that pitted Boston police against Massachusetts state police. "Having procured a jack-hammer as well as several hard hats and other construction-related paraphernalia, he and a group of fellow students cordoned off a section of street in downtown Boston and went to work, as it were, tearing up the pavement," the report read.

From there, things got pretty complicated. "O'Brien then reported his own crime to the Boston police: college students dressed as construction workers were jack-hammering in downtown Boston ..." the report continued. "His handiwork only half done, O'Brien then telephoned the Massachusetts state police. He and his fellow construction workers, O'Brien said, were trying to do their jobs but were being harassed by a bunch of college pranksters dressed as policemen. In short order, the Boston police came to arrest the students and the state police came to arrest the Boston police."

Weirdly, O'Brien was also behind an incredibly elaborate prank pulled on Bill Cosby, which he later told Howard Stern was really just an attempt to try to get to meet the comic. After convincing Cosby he was going to be awarded a Lifetime Achievement in Comedy award from the Harvard Lampoon, he ended up getting Cosby to fly in for the "ceremony", and picked him up in his parents' garbage-filled, rather ancient station wagon. The award itself wound up being a "slightly altered" bowling trophy.

Despite the awkward pick-up and prank, Cosby apparently took it all in stride. "I think he cherishes [the award] to this day," O'Brien said, according to "Someone recently found pictures of me looking like a 19-year-old woman. He's holding the bowling trophy and smiling and it's night."

He was stalked and harassed by a priest for months

In 2007, Rev. David Ajemian, a priest with the Archdiocese of Boston, was arrested and charged with aggravated stalking and harassment after repeatedly sending O'Brien bizarre letters for months. "Is this the way you treat your most dangerous fans?" Ajemian reportedly wrote in one letter after he was turned away from a taping of one of O'Brien's shows. He also referred to himself as "your priest stalker" in another note, according to CBS News. The New York Times added that Ajemian wrote in one letter that he had been following O'Brien's career since they were both students at Harvard.

According to My Fox Boston, Ajemian—who was arrested again in 2010 in connection with stalking another television host—eventually pleaded guilty to disorderly conduct and ordered to stay away from O'Brien. He also sought treatment at a mental health facility at the request of the Church, but voluntarily checked out shortly thereafter. Speaking in 2010, Ajemian downplayed the threats he made in his letters to O'Brien, claiming, "I think that if I thought I could get an extra ticket, go into the audience, he would recognize me and perhaps find the whole situation somewhat amusing." Right, okay.

He's been accused of stealing jokes

In July 2015, O'Brien was targeted in a lawsuit by a San Diego man named Robert "Alex" Kaseberg who claimed that O'Brien had stolen multiple jokes he had posted online and used them in various monologues on his show. The case remains ongoing to this day. In fact, in October 2016, Kaseberg amended his original complaint to add a fifth joke he alleged was stolen by O'Brien and his team. The defendants deny Kaseberg's allegations, according to the Hollywood Reporter. Now, that's no laughing matter.