Dogging the Wag 2: Trials of a Laffmeister
The following is culled from an article in the September 12, 2003, issue of Entertainment Weekly:

"The last 10 years have been like a Bataan Death March that ended at a Dairy Queen," notes [Conan] O'Brien. "Long, arduous, difficult -- but ultimately happy and refreshing."

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"The perfect world would be where The Conan O'Brien Show would be on, and you'd be reading my short story somewhere and wearing my designer jeans," O'Brien told The Harvard Crimson upon graduating in 1985.

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He [O'Brien] applied to write for Late Night with David Letterman in 1987 -- but was rejected.

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Robert Smigel [Conan's first head writer]: We were getting bad reviews fairly quickly, but at the same time I was getting congratulatory phone calls from people in comedy. George Meyer, legendary Simpsons writer [and former writer for Late Night with David Letterman], calls and he's like, "Amazing. You guys figured out how to replace Letterman. It's completely original and funny." And at the same time we're hearing "This is a disaster."

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O'Brien: People can say Wow, you suck at sports, or your hair is weird, but if someone says you're not funny, that's the thing that would hurt me the most. For a year there, it looked like I could become famous as one of the most unfunny people ever, and that was the nightmare. I was in a sinking car that was going to the bottom of the ocean and I was getting out of that car. I was not going to become famous for being unfunny. I'll cudgel America into accepting me.

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[In April 1995, Conan hosted the White House Correspondents' Dinner.]

O'Brien: It's a tough, tough room and I just started killing. Clinton was pounding the table and his face was red and he was crying. The next day I felt like I had taken a backpack off. [Studio] 6A seemed smaller and more manageable.

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Last year, O'Brien signed another lucrative deal, earning him an estimated $8 million a year. But his contract expires in December of 2005, raising the question, Will he be ready to replace Letterman or Leno one day in the 11:30 slot?

O'Brien: People think you've got to move earlier and earlier to 11:30. But my theory is, like Batman, I want to move deeper and deeper into the night. Carson Daly will be confused because I will pass him going the other way. I'll get his 1:30 show and then I'll go to 2:30 and then 3:30 and by the time I'm a very old man, I'll have a mildly popular morning show in Miami. Andy and I will be just sitting there on stools with pink coffee mugs that say "Mornin' with Conan and Andy" and we'll have a houseboat that we both live on and we'll solve crimes on the side. Yeah, it's going to be good.

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Here is The Onion A.V. Club's May 2001 interview with Conan.

An excerpt:

Conan: I think people came around to our sense of humor, but initially, I don't think all the criticism was wrong. Maybe in the severity, but I wasn't nearly as good a TV performer as I am now. I got a lot better, and I learned how to just be myself and do all that, whatever, muttering, and those asides, and make those observations. I learned how to just do that and be the way I am with my friends in a very unnatural situation. I think that's the part of doing these shows that no one understands. The trick to them is not to become a funny guy. You have to just be that from the beginning. The trick of these shows is figuring out how to be the person you always were in an unnatural situation, with five cameras staring at you, and with an audience sitting there, and lights, and celebrities you've never met coming out.