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It was one of the biggest laughs of my life. At 19 years-old, I had the good fortune of scoring free tickets to see a taping of Late Night with Conan O’Brien, then at the height of its stature in both the world of comedy and the culture at large. Personally, it was a major moment considering that I wore Late Night merch to high school on a regular basis. (Surprisingly, this did not get me laid.)
The same way some kids looked up to baseball players, he was an idol to me, and the coolest person imaginable. As a result, I never missed a single show. Since it aired way past my bedtime, I’d hit record on my VHS player every night I went to sleep, and then fast-forwarded to the 12:30 a.m. hour when I got home from school. Of course, I'd rewatch classic sketches ad nauseam. I also have vivid memories of friends and family rolling their eyes at me one summer because I wouldn't stop reading fake predictions out loud from the companion book to the show's popular segment, "In the Year 2000." (Example: “It will be revealed that carrots will not actually improve your eyesight. But they are still number one when it comes to scratching a deep rectal itch.") In other words, I was a member of the Late Night hive—a Conan stan, years before the figure of speech came into vogue.
On the night I attended the taping, the guest was show favorite Tom Hanks, and the musical guest was a typically idiosyncratic act, Wolfmother. As the evening taping wrapped and the audience was readying to depart, O'Brien said, in preparation for a future airing, that he wanted to show us something first. For a fan, it was like a surprise bonus. Not only would I have sat in NBC at Studio 6A all day, but I would have moved in.
What began playing over the monitors was what’s dubbed a ‘remote’ segment, a taped bit where O'Brien would go out in the wild with a camera crew. If David Letterman pioneered the concept of these remotes (like when he worked the drive-thru at Taco Bell, warning customers he’s just getting over a stomach flu), O'Brien perfected them right away. Quick on his feet, and always armed with the perfect joke, the humor was always aimed squarely at either his surroundings or himself. Most importantly, it was never at the cost of who he was with.
This particular remote featured O'Brien and his former roommate Jeff Garlin visiting the old apartment they shared in Chicago when they were both fledgling comedians in the late 80s. O'Brien buzzed up, surprising the current resident, and proceeded to poke fun at the concept of a celebrity returning to their old stomping grounds, while noting the other incredible things that may or not have happened inside this feeble walkup. “The horse Seabiscuit died in this room,” O'Brien explained, the jokes coming fast and furious. “Penicillin was invented in that bathroom,” he added, while talking to his former landlord. “You’re the one who said that if you grow that mold it might inhibit bacterial growth.” It was the perfect example of a deft sense of humor—a blend of both extreme absurdity and intelligence. O'Brien's old landlord, completely unfazed, explains there were actually a lot of famous people who lived in his buildings over the years. Like who, he and Garlin incredulously asked? “The Cubs’ physician's daughter,” he replied, walking directly into the regular self-deprecating shtick that O'Brien, too, isn't so famous. By the end of the bit, a plaque is nailed to the wall for it to forever be known that it was once the home of Conan O’Brien.
I’m feeling nostalgic about that show this week, as O'Brien prepares to wrap up the nightly format of his talk show after nearly three decades and three different iterations. He's now headed to HBO Max, where he'll presumably (and hopefully) be doing more remote bits like the apartment one. But as Conan embarks on his next venture, I can’t help but think about the fact that his trajectory has been unlike any other host’s in late night television history. His rise is an oft-repeated tale which will still be told hundreds of years from now; comedy fans huddled around whatever futuristic devices will speak of his legend.
Following stints as a standout writer on both Saturday Night Live and during the golden era of The Simpsons, Late Night with Conan O’Brien premiered in September 1993, when he took over the reins from David Letterman. (The summer before, Esquire introduced readers with a “premature oral history” of “the young carrot topped guy with the weird name.”) The cold opening of O'Brien's debut episode took on the pressure of the new job head-on. In the bit, O’Brien nonchalantly walks to work as absolutely every form of life encounters slyly mentions the big shoes he’s attempting to fill. As he’s leaving his apartment, his doorman says “Lotta pressure!” A man selling flowers: “You better be as good as Letterman!” The front page of the paper he buys: “CONAN HAD BETTER BE GOOD.” Girls playing hopscotch tell him he “better be good,” and a carriage horse even manages to neigh the words, “Lotta pressure!” The bit culminates in Conan walking into his dressing room to prepare to cheerfully hang himself, only to be interrupted by his call to get to the stage to start the show. (Would that punchline be eviscerated in today's cultural economy? Probably.)
The critics were bloodthirsty, and O’Brien was raw meat. “The young man is a living collage of annoying nervous habits,” wrote Tom Shales of The Washington Post. “He has dark, beady little eyes like a rabbit. He's one of the whitest white men ever.” The ratings weren’t much better. With zero confidence, NBC was ready to pull the plug on a routine basis, renewing the show a mere 13 weeks at a time. Each time, O’Brien persevered and turned things around. Ultimately, I think it helped polish him. A new generation began to see themselves in the show’s irreverent humor; equal parts smart and joyfully silly, deeply unique and positively unafraid. With nothing to lose, the comedy pushed limits in the subtle craft of silliness. A comedic voice was perfected, a sharp interview style came into fruition. The guests grew in stature, as did the ratings, and simultaneously the show became a showcase for the burgeoning scenes of alternative comedy and indie rock which were sprouting up alongside it. By 1996, Rolling Stone called Late Night “the hottest comedy show on TV.” By then, I was judging friends by whether or not they watched Conan.
Everything was hunky-dory. That is, until O’Brien’s well-deserved promotion to The Tonight Show, first announced in 2004 and enacted a full five years later. What transpired was a classic mess that garnered national headlines and found him back in his former position as the underdog, with former host Jay Leno ready to step back into his old time slot. After an organic fan-led movement which even included protests and rallies, O’Brien departed The Tonight Show on his own volition, a show of supreme strength. Even then he refused to succumb to the perceived failure—O’Brien took the high road by famously saying on his final Tonight Show episode, "Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you're kind, amazing things will happen.” Eschewing giving a public middle finger to NBC, O’Brien gave us a lesson in civility, along with sentiments that might as well be printed on a mug.
What followed was a vaudevillian national tour to greet his nation of fans, a digital media empire, and a nightly show on TBS which allowed him to host a show completely on his own terms. In the final months of Conan, he used his resources to aid the Largo Theater in Los Angeles, moving the show into the small space to help it survive the pandemic. Eerily, he even jokingly predicted this very endpoint in his very first episode of Late Night. “Most guys who are in this spot, they came up here a different way,” he said, in his second monologue joke ever uttered on television. “A lot of guys spend years and years in the clubs, working very hard, struggling, and finally get here on TV. My plan is to start on TV and claw my way into the clubs.”
O’Brien could have done anything with Conan, but in a direct reaction to the Trump years and disturbed by a bubbling xenophobia, he used his platform to produce a series of travel specials to introduce Americans to the human side of other cultures, dubbing it Conan Without Borders. When Trump was stoking fears of immigration and border walls, O’Brien went to Mexico. Immediately after Trump reportedly called Haiti a "shithole" country, Conan went there too. And in an effort to raise awareness about the Armenian genocide, he devoted an episode to visiting that country as well.
Now, aside from that brief gap in 2010, viewers won’t be treated to a daily talk show hosted by O’Brien for the first time since 1993. And while we sure have a hell of a lot of other options, there will never be another regular distinctive daily voice quite like O’Brien’s. We won’t be treated to a daily monologue or his famous string-dance, Conan using his physicality, including towering height and bright red hair, to masterful effect. We’ll be missing his trusty sidekick Andy Richter and his perfect quips. And we’ll miss a trademark fetishization of silly intelligence, with Conan reminding us not only to never forget to be foolish no matter how hard one works, but also that those two things can even go hand-in-hand to beautiful effect.
So until his HBO Max show premieres on some unknown date, and in whatever form it takes, I’ll still be wearing my Late Night merch proudly. Regardless of whether or not it gets me laid.
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