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When Conan O’Brien — a 30-year-old Harvard-educated writer who’d worked on The Simpsons — was tapped in 1993 to replace David Letterman as host of NBC’s Late Night, the general reaction was, “Who?” Twenty-eight years later, the 6-foot-4 comedian, with the swooping red hair, becomes history’s longest-running late night host when his TBS show, Conan, broadcasts its final episode June 24 after a decade on air. Beside him for much of the journey was Andy Richter, who originally was brought on as a Late Night writer.
“I picked a deli in Westwood,” recalls Richter, 54, of his first meeting with O’Brien. “We just hit it off. I mean, we’re the same kind of stupid.”
It was head writer and Saturday Night Live veteran Robert Smigel who thought Richter might be well suited to fill the Ed McMahon role. “There was a camera test, and Robert said, ‘Hey, just go sit by Conan and keep him company,’ ” recalls Richter. Despite some inspired early guests (John Goodman and Drew Barrymore joined the premiere; Radiohead played on the second episode), O’Brien and company suffered from jitters, and critics were not kind. (“For at least on opening night,” wrote THR in its pan, “[Conan] as well as his network seemed largely in the position of being scared witless.”) But, fueled by segments (“In the Year 2000,” “Desk Drive”) and characters (Pimpbot 5000, the Masturbating Bear) that indulged O’Brien’s love of the absurd, the show found its footing and drew a loyal audience of college-aged comedy lovers. So much so that O’Brien was bequeathed The Tonight Show in 2009 — a reign of just seven months, as NBC had second thoughts and restored Jay Leno to the 11:35 p.m. slot with a 30-minute show, pushing O’Brien past midnight. O’Brien quit (albeit not without a $45 million settlement).
“We weren’t really given a chance,” says Richter, who had returned as Conan’s sidekick on Tonight after leaving Late Night in 2000. “I don’t see Jay Leno or Jon Stewart or Letterman, or even Colbert, having a masturbating bear or a robot that’s a pimp. Our show is full of nonsense like that. And I’m pretty proud of that.”
Richter shared more thoughts on the Conan O’Brien legacy with THR.
How did you originally get the job? How did you get chosen to be his sidekick?
I knew Robert Smigel through a friend that was a castmember on SNL back whenever that was ’91, ’92, something like that. And then I met Robert. I was in LA, doing a stage show that we brought from Chicago called The Real Live Brady Bunch. And Robert was here in the summertime. We just hit it off. Then he called me and said, “Hey, this guy that’s replacing Letterman is a friend of mine, and I’m going to be the head writer on the show. Would you want to meet him to possibly get a job as a writer on the show?” And I said, “Sure.”
But then to go from writer to his Ed McMahon, I mean, that’s a huge leap.
There were about three months of preproduction before the show aired, and we already had established a comic rapport around the office. I didn’t even realize that I was being groomed to be the sidekick, but when Conan started doing tests. Dave wasn’t even gone yet. They were still shooting shows while we were up on the ninth floor, writing and trying to conceive what we were going to do.
There was a day where there was a camera test, and Robert called me and said, “Hey, will just go sit by him and keep him company?” One day they brought in a chef to do a cooking demonstration, and I was there for that. They just had me sit next to him and talk to him, and that just sort of built the beginning of the banter. And then when we started to do test shows with audiences, Robert asked me if I wanted to be the sidekick, and I hadn’t considered it. And I was kind of like, well, I don’t know. And then I thought, “Who am I kidding? I get to be on TV every night. Sure. I’ll do it.”
What do you remember of the first episode?
I remember at the end, Conan sang a song and then Tony Randall came in to join him in the song. It was my first time meeting Tony Randall. And I met Tony Randall a number of times after that. He would come on the show, and I would notice that he always wore suits with linings that matched the pocket square and the tie. They were all sort of like Garanimals of beautifully tailored clothes.
We had a party afterward at the 21 Club. And I just remember, just hanging out with John Goodman. After the show shot, it went pretty well. We were all pretty elated, this new thing. I come back to my desk, and there was a beautiful desk clock, a gold desk clock from Tiffany’s on my desk in a box. It had a card in it that said, “It’s been a pleasure working with you, Lorne Michaels.” Which I guess is kind of classic Lorne, because it’s your first night, and you read that, you think, “Oh, shit, am I fired?”
He could’ve said, “I’m so excited for our journey ahead.”
“Here’s to many more.” But no, “It’s been a pleasure working with you,” all past tense.
I really enjoyed your weird sketches. Sometimes I’d be half asleep and not sure if I had dreamed it or not.
We did a lot of really excellent non-sequitur stuff. My favorite one was “Satellite TV.” We said that we have this satellite system that allows us to get all these channels that aren’t available to the public. And then they were all just nonsense. I think one was called “Lincoln Climaxing,” and it was just a Lincoln lookalike having an orgasm in slow-mo and soft focus.
So when you guys went to primetime for Tonight Show, that was so exciting. And then the way it all played out was so horrific, I mean, to a fan, to watch it. And I’m wondering what it was like on the inside.
It was very stressful. There was this kind of notion of, “Can the Conan show cut off the rough edges and make itself more palatable to elderly people, in an hour-earlier time slot?” So we already had that kind of pressure. And then they had given Conan the deal five years before and Jay Leno had agreed to it. And then he backed off the deal when it came time for us to do the job. And NBC wouldn’t commit, they wouldn’t commit to one or the other. And then they came up with this cockamamie “Jay will do a half an hour after the local news and then Conan will do an hour.”
We knew that that would just mean that Jay would eventually take The Tonight Show back. We weren’t really given a chance, because Jay was there. And Jay was Jay, and he already had their ear. He already had a viewership at that time slot. So there was no real chance for us to grow. I went from being like, “OK, now I’m on The Tonight Show ” — like a tenured professor of television — “I’ll be here as long as I want to be,” and then it vaporized in seven months. And it was strange, too, to realize that we were becoming, like, a cause — people congregating outside the building, chanting support for a comedy show — and then also that we were part of broadcast history. That was a strange, strange development.
So now that it’s wrapping up for good, officially, what are your feelings?
It’s a little sad. Mostly, what we’re feeling now is a celebration and, just, pride. I mean, I do feel one of the best things about our show is that we meant something to younger people, people younger than us that were serious about comedy in the same way that the shows that meant something to me when I was in my teenage years, my college years, and thinking about, “Maybe I want to do comedy for a living,” that we made an impression on people like that and helped form their senses of humor and what they wanted to do with television when they got a chance to do something with television.
And what comes next for Andy Richter? Do you remain in Los Angeles?
My kids are here and my life is here, so, yeah. I mean, truly, nobody knows what’s going to happen. There’s this HBO Max deal, but nobody really knows what’s going to happen with that. So I’m developing an animated show. I’m attached to a game show that’s being pitched. I actually direct TV commercials, and I’ll have a lot more time to direct those. One thing that the last 10 years have been in short supply of is for me to get to act as much as I would like to. So I have the freedom to do that now.
A version of this story first appeared in the June 23 issue of The Hollywood Reporter magazine. Click here to subscribe.
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