To be totally honest, I haven't seen much of “Late Night with Conan O'Brien” since I started working full-time—the show starts at 12:30 am EST and I'm usually asleep much earlier than that. Because of this, maybe the show should be a bit lower in the standings, though when I was a die-hard viewer (college and the first few years out of school) there was no funnier hour on TV.
O'Brien first came to the public's conscious (or at least the comedy nerd's conscious) in the late 80s as a writer and bit performer on “Saturday Night Live” before moving on to a writer/producer role at “The Simpsons”. There was no doubt that he was a hilarious writer—some of his episodes on “The Simpsons” are the classics that most refer to when speaking about the “good old days” of the show—but people had no idea who this extremely tall, extremely Irish looking guy welcomed them to David Letterman's old show in September 1993. The only thing that they knew was that O'Brien was no Letterman.
And that was ok. Despite attempts by NBC to hire Garry Shandling, Dana Carvey, Jon Stewart or Drew Carey for the job, O'Brien won out. O'Brien's old boss at SNL (Lorne Michaels) was producing the show and felt that the upstart had something that people would like. Having an established house would have been the safe play, but the show after “The Tonight Show” is supposed to be hosted by an anonymous person. Letterman did it that way and he was hugely successful. And when Conan leaves to host “The Tonight Show” in 2009, it should be the same way.
Unfortunately, for the first few years, it didn't look as if O'Brien would be so lucky. NBC had the brilliant idea of just signing him to 13-week contracts, which probably made his confidence soar, and were close to firing him—only they couldn't find a replacement. Like many things in life, luck and the ability to work cheaply (and on a ridiculously short contract) were the saving graces of a now successful man.
Somewhere after the awkwardness of hosting his show dissipated, O'Brien found his confidence and started doing comedy his way. And that's when he started to shine. He was one of the first mainstream comedians to bring “nerd humor” into American living rooms. And while that's not on par with Richard Pryor, Lenny Bruce or George Carlin bringing their edgy brand of funny to the masses, it was an important step to where we are today in terms of what our nation finds funny. Quick aside, when I say “Nerd Humor” it's a catch-all reference to jokes about “Star Wars” or “Star Trek”, general awkwardness or any self-deprecating jokes.
For the first seven years of the program, O'Brien had his own Ed McMahon in the form of Andy Richter. We've spoken a bit about the genius that is Richter in a previous entry, but he really made his bones on this show. Whether it was a weekly staring contest bit with O'Brien, except for Richter's last episode Conan always won because there would be something strange or disgusting occurring behind O'Brien that would break Richter's concentration, or going for a desk ride, this is where Andy and Conan would pretend to drive around while a green screen behind them showed the audience where they were heading, Richter always brought the funny.
And that was important for the first couple of seasons because while an unknown himself, Richter was a crutch that O'Brien could lean on when the show was going off the tracks.
In addition to Richter, O'Brien also played off his band leader and former member of Bruce Springsteen's E-Street Band, Max Weinberg. Weinberg was always at his best when O'Brien would make him out to be an arrogant, sleazy character who would do anything at any time to get ahead at work or with the ladies. With his sly smirks and man-of-few-words demeanor, Weinberg quickly became an audience favorite, who were in on the obvious joke.
Ultimately what saved O'Brien was the comedy, it was terrific stuff that hadn't really been done before and just needed a chance to find an audience. And it did, after three year O'Brien began to get more recognition from the mainstream press who hailed him a favorite of Generation-X and especially college students. When the mainstream recognizes hidden genius this is normally this is the kiss of death for hipsters and young people who hopscotch to the next fad, but O'Brien persevered and both the underground and the “normal” public both enjoyed him.
Though O'Brien, Richter and Weinberg were funny on their own, there were a large cast of characters who'd visit the set nightly. Some real (Tony Randal, Abe Vigoda) some fictional (Pimpbot 2000, a stereotypical 1950s looking robot that was programmed by a stereotypical 1970s pimp and Triumph the Insult Comic Dog) but always killer. The one classic bit that stands out in my mind was during the winter of 1996: O'Brien was on a quest to find Grady character (Whitman Mayo) from “Sanford and Son”. A few times a week he'd play an old clip or two of Grady from “Sanford and Son” and then show a map of the United States and fake callers would phone in with recent “spottings”.
As the months passed, the bit grew more and more popular and finally the show had to find the real Grady and began promoting that he'd be on that Thursday night's show. Up until this point, I doubt that anyone had thought of Whitman Mayo in 20 years, but the crowd was going crazy for this guy when he showed up. A gigantic flashing, neon sign that said “Grady” dropped from the ceiling, confetti flew everywhere and the band played the theme to “Sanford and Son”. The crowd reacted as if Mayo was the first man to land on the moon, come back to Earth and hit a walk-off grandslam in Game Seven of the World Series.
The genius behind this bit was that O'Brien and his writers took a character that we all knew, that was buried deep in our collective memories and brought him back. I've said it before, you can not go wrong with nostalgia. But it was more than that, the two-month build up that slowly started gaining steam was tremendously well-done. Normally, my roommates and I went out to a bar every Thursday night to try and pick up chicks, there was no way in hell any of us were going out that night. Any time you can stop a few college guys from trying to drink beer and find girls, you know you have something special.
As the show and the host matured, certain things got better: O'Brien's opening monologue went from brutal to well done and his interviewing skills got remarkably better as well. The one thing that O'Brien was terrible at was interviewing guests. He would ask a question and as the guest was answering, O'Brien would start interjecting pointless stories which would infuriate the tale's teller. This wasn't done with any malice, like Ali G or Tom Green, I think it was done out of general nervousness and the fear that if O'Brien wasn't talking, people would forget whose show it was.
It was always my opinion that if the show was cancelled in its early years, that would have been the reason. To their credit, NBC stuck with the show and it prospered. This should be a lesson to all TV executives who want to cut down an interesting, new show. Give it time and it will work, the American people don't like crap, but if that's all you give them, that's all they'll watch.
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