Conan O'Brien: Like You've Never Heard Him Before

From Battling depression to playing the ultimate prank on disgraced comedian Bill Cosby, the late night star shared it all with Howard

The great Conan O'Brien hasn't stopped by the Stern Show studio in a while, but he made his triumphant return this morning and he gave one of the best interviews you could ever hope for.

From hilarious stories from his past to serious discussions about his battles with depression it's Conan O'Brien like you've never heard him before!

And make sure to see Conan like you've never seen him before when he broadcasts his show from Cuba! Watch Conan in Cuba, Wednesday, March 4th, 11p EST on TBS!


When Conan was a young kid at the Harvard Lampoon, he really wanted to meet Bill Cosby. How do you meet a comedic legend (before the fall) when you're just a kid at Harvard? You create a fake award and give it to him – he'll show up in a tux!

Conan met Cosby and his entourage in his parents beat up station wagon and Bill had to move a McDonald's wrapper over just to take a seat.

Naturally, an award is an award and Bill accepted it.


Conan really opened up to Howard when he volunteered he's someone - like many Americans - who battles depression, sees a psychiatrist and is on medication. Like we hear from so many funny people, Conan feared that he needed to be depressed to be funny, but at a certain point in his life he realized he just wanted to be happy.

Listen to the intimate, honest conversation below.


Before becoming a Late Night icon, Conan was an unknown (to the public, anyway) writer on Saturday Night Live.

He wrote sketches like 'Mr. Short Term Memory' and a favorite of Howard's, 'Nude Beach'. He yearned to perform but he wasn't jealous of the performers on his cast of Saturday Night Live – he couldn't do what Phil Hartman or Dana Carvey did.

Watch Mr. Short Term Memory:


Conan moved onto The Simpsons after SNL and wrote one of the classic episodes in Simpsons history - Marge v The Monorail. Our own George Takei, but he turned it down because he felt the episode made fun of transit and he was on the board of the Southern California Rapid Transit District. The part went to Leonard Nimoy.


Conan harbors no animosity toward NBC, owing in part to the fact those directly involved with the end of his tenure on the Tonight Show are no longer there.

He's reluctant to talk about the Tonight Show situation because he really feels his career has been a lucky and fortunate one and he doesn't think people in show business should whine.

CONAN IN CUBA! the idea is 'too perfect'.

Over 20 years in late night and Conan is still an innovator. Just days after our relationship with Cuba changed, Conan knew he had to do a show from there. Don't miss it Wednesday, March 4th on TBS!