Conan O'Brien's Career Was Almost Over Until This Famous Guest Star Came Along

In 1981 O'Brien attended Harvard University with designs of being a doctor or a lawyer, but within that same year he started writing for one of the most prestigious comedy birthing grounds: the Harvard Lampoon. He went on to become one of the few people voted as editor of the Harvard Lampoon for two consecutive years. 

In a 2011 interview with Marc Maron on his podcast WTF, O'Brien said he would never have taken up comedy without the Harvard Lampoon, where he met people who would go on to be writers for Saturday Night Live and The Simpsons. He described the Lampoon as "the Skull and Bones of nerdy, self-effacing comedy geeks":

[I] met some really smart people there, [and] some dumb people there. It's a big melting pot. It was no surprise to me when they caught the Unabomber and he turned out to be from Harvard.

Just before David Letterman ended his tenure as the host of The Late Show with David Letterman, O'Brien gave a monologue about how Letterman's appearance on Late Night saved the show in '94. O'Brien explained how after he took over the show everything started going wrong and that the "network started to make it clear that [he] probably wouldn't be around for very long."

A few months into the show, Letterman sent a message to O'Brien saying he wanted to appear on Late Night as a guest. O'Brien believes his appearance turned the entire show around.

"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," O'Brien recalled of the experience.

The late night host told Rolling Stone that during his Saturday Night Live days in the '80s and early '90s he would sneak down to Studio 6A, where David Letterman filmed, and sit at the host's desk to write material. This was the same studio where O'Brien would later host Late Night.

O'Brien said at the time he had no dreams of taking over the chair, and that his breaking and entering simply served a functional purpose:

It was more like, "This is where he sits? Cool"...  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.

When he lost The Tonight Show, O'Brien put on a brave face, but afterwards he became a mess. He went on a tour with his band and some writers, but when he finally had to face life at home without a show, he felt "'like [he'd] just been in a car accident." He said upon returning home for good, he felt "a crazy mix of elation, anger, sorrow. Con­fusion was a big one."

His wife, Liza Powel, remembers him "in the house all the time," constantly walking from room-to-room looking for something to do. She told Rolling Stone:

I said, "This can't last - it'll drive us crazy!"... He was so sweet about it, and I felt like such a jerk. But seriously, I almost rented an office for him.

Before O'Brien hosted Late Night, he worked as a comedy writer in Los Angeles, CA, where he wrote for The Simpsons. During his short tenure on the show, O'Brien wrote fan favorite episodes "Marge vs. the Monorail" and "New Kid on the Block." 

Even though those episodes went on to be some of the best the show ever released, O'Brien was still a ball of nerves while writing on the show. To endear himself to the other writers, he performed gags to make everyone laugh. O'Brien told The Simpsons: An Uncensored, Unauthorized History:

There was one where I would go to the refrigerator and and I'd get a Coke and I'd fill my mouth with Coke and then I'd start twitching... the Coke would foam up and come out of my mouth and it looked like I was having this horrible fit. And I don't know why... but people really enjoyed it.

In an interview with Vanity Fair, O'Brien explained his love for the character, saying how Mr. Burns possesses three qualities "perfect if you're a comedy writer:" old age, riches, and an evil persona. According to him, those traits make him a character with limitless comedic potential.

When O'Brien first began his tenure on Late Night in 1993, it took a while for the show to find its sea legs. Executives at NBC reportedly revisited their position on the show on a weekly basis. The company's back-up plan? To put actor Greg Kinnear into O'Brien's spot. 

Kinnear was already hosting Later, the show that followed Late Night, and was NBC's initial choice to host the show. As history shows, O'Brien ended up bringing in big numbers and "Option K" never needed to be instated. O'Brien's producer Jeff Ross told Rolling Stone, "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."

Critics appeared united against O'Brien, but, in the word's of O'Brien's sister, "at least his name [was] still in the paper."