Conan O’Brien: Weirdo to Weirdos — An Appreciation Thread

As far as we know, this is Conan O’Brien’s last night as a late-night talk show host. He’s closing up his show Conan on TBS to transition to a new project on HBO Max…but that’s being called a “variety show,” whatever that means anymore. 

He’s been on TV interviewing celebrities for just short of 28 years (give or take a few notable temporary hiatuses), and Wikipedia says he’s the “longest-working of all current late-night talk show hosts in the United States.” That probably checks out, but it feels strange: I think even people like me who have grown up with Conan1 still see him as this kind of plucky underdog figure, but he’s actually the Old Man of Late Night.

I started watching late night in the early ’90s. I was pretty young, but I remember sometimes seeing Johnny Carson in his last years and stayed up for his last show, and the first battle for The Tonight Show is something I recall hearing and reading about. Jay Leno and David Letterman formed such an obvious yin and yang that it’s easy to be reductive about it. If you liked Letterman, you liked his irreverence and daring to do the unexpected, and you thought Leno was toothless and lowest-common-denominator. If you liked Leno, you liked his well-oiled machine of a show and his geniality and grace towards his guests, and you thought Letterman was grouchy and unpleasant and couldn’t understand why he wasted so much of the audience’s time on purposefully weird and aimless tangents. In real life, the majority of people probably just watched whichever one had the guest on they wanted to see that night, but there were a bunch of writers in the media who were too young to get to pick a side in the Lennon vs. McCartney wars of the ’70s and now had a similar narrative they could sell.

If we take Carson’s Tonight Show as the format of the “traditional” late-night talk show host, Leno’s Tonight Show was a minor update for the ’90s: a little slicker, a little hipper, but basically still a friendly face inviting Hollywood into your living room after a few quick zingers. 

By contrast, Letterman, since his early days following Carson on Late Night, adopted the persona of the above-it-all, too-cool-for-school outsider. Let’s go hassle the phonies on The Today Show. Let’s go talk to some weird locals we found. Let’s see animals doing goofy tricks, and it won’t matter if the tricks don’t work. Stunts like strapping on an Alka-Seltzer suit and dunking himself in a tank of water were partly about showing off how much of NBC’s money and airtime he could waste on stupid things. If there was an artist’s statement to the show, it was to challenge the late-night format by finding mundane weirdness, putting it in front of a camera, and saying, “But maybe this is entertainment?” 

Conan O’Brien’s Late Night was also a sort of a deconstructionist alternative to the Tonight Show format: a reliance on oddball visuals, non-sequiturs, and self-deprecating humor. But Conan didn’t have the same disdain for showbiz that Letterman did. His show would be a celebration of artifice instead of a rejection of it. Instead of finding weirdness in the world, Conan and his writers and performers would create it. 

And so, although it had the basic shape of The Tonight Show, a lot of the time Conan’s Late Night was more like a sketch comedy show that spilled into a show where a guy at a desk talks to celebrities. Conan played a sardonic straight man to a lot of these bits, as though he had put on his nice suit and gone out that night intending to put on the best darn traditional talk show, but he kept getting interrupted by masturbating bears and robotic pimps that were somehow beyond his control. The conceit of the show, I often felt, was that he was attempting to do The Tonight Show but inevitably failing. 

And then guess what happened!

In the second battle for The Tonight Show, it’s easy to paint Conan as being utterly screwed over by NBC and by Jay Leno. Maybe he was. 

I can appreciate, on some level, that NBC was in a bind: they had one well-established guy still at the top of his game ratings-wise and one rising star with nowhere to go with that momentum without bailing to another network. It’s a hard choice, but it seems like the thing to do would have been to cut one of them and get it over with, then move forward. But I guess it’s not my money; if it was, maybe I would’ve also tried shuffling and reshuffling my latest crazy plan every couple months in the off chance that maybe everybody would stay on my network and be happy and I wouldn’t have to be the bad guy.

I was following the whole thing very closely as it unfolded, primarily via articles on a once-semi-prominent Onion-adjacent pop culture website. I never frothed myself up to full “Team Coco” tribal rabidness, but you know, I thought Conan was funny and didn’t think Leno was funny, and I felt my dude had gotten a raw deal. But even I could see there were two problems with Conan on The Tonight Show.

One was that Conan had a terribly romantic notion of what it meant to be a broadcaster hosting The Tonight Show, which he saw as a venerable, almost sacred television institution. This was the ultimate accomplishment for him, something he’d wanted and worked for, the brass ring, first prize at the fair. But secretly, the demographic that loved Conan, by and large, did not actually really give a shit. The Tonight Show name didn’t carry any significant cultural cachet or mystique for the younger members of Team Coco. Even me being a bit older and remembering Carson, I knew that a lot of what made The Tonight Show such a big deal is that it was basically the only game in town in those days; by 2010, the late-night field was more crowded and the audience was more segmented, and most guests promoting their projects would just sort of make the rounds and hit all the big shows anyway. So a lot of us on the pro-Conan side had this feeling of, like, Why don’t you just walk away and do a different show? What is the big deal about The Tonight Show, actually? It became frustrating, like your friend telling you about how awful their relationship drama is and then getting mad at you when you say they should try dating somebody else.

But the other and more serious problem was that no matter what NBC did behind the scenes, Conan got to take his shot, and people didn’t go for it. A larger number of television viewers just fundamentally liked Leno better, and at some point, you can’t fight that. Team Coco often painted the Leno fan as some sort of troglodyte incapable of appreciating the more sophisticated or cutting-edge comedy that Conan offered, but honestly? I don’t think it’s right to characterize Conan O’Brien as the smarter choice. He was the weirder choice. That is, in fact, the whole reason that you like him, is it not? The Tonight Show audience in 2010 enjoyed a polished standup being a bit of a wiseguy but not too mean right before bed. The Tonight Show audience today enjoys an amiable goofball playing games with celebrities right before bed. That audience did not and does not want to tuck in with a hyperaggressive weirdo at the end of a long night, and though you or I might not agree with this choice, it’s hard to say it’s an objectively wrong one.

So Conan had massive goodwill from a very public media battle in which he was portrayed as The Good Guy, then went on to do a hugely popular tour. Then his new show started, and the momentum kind of stalled. A lot of people will say this is because the show was on TBS and it was kind of an embarrassing step down, but again, I don’t think the prime Conan demographic really cared. I think the disappointment came from the fact that NBC and The Tonight Show and the traditional late-night talk show format in general had come to be seen by the fans as this straightjacket keeping Our Hero down, and now that he had burst free of these shackles in triumphant glory, he could finally cut loose and do what he really wanted to do!

But what he wanted to do was the same kind of show he had been doing all along, just over here now. He liked the format, seemingly; he liked the structure, if only because it gave him something to push against. He’s comfortable with it. Conan O’Brien is 58 years old. On his podcast, it’s kind of a recurring bit that he acts bewildered by what a podcast even is; he says, “If you’re just tuning in…” and Sona makes fun of him because that’s not how people listen to podcasts, and we all laugh, but I think that honestly shows where his instincts are, and can you blame him? When he first got into television through such unlikely circumstances in 1993, the standard late-night format was all there was, but it’s a format that’s increasingly irrelevant in 2021. Leaving this format is the right decision and long overdue, but I can appreciate how difficult it must be.

I don’t have HBO Max, and I’m probably not going to get it anytime soon. I listen to podcasts, but not as frequently as a lot of people my age do, and so it’s not unusual that I get weeks behind on Conan O’Brien Needs a Friend and decide to cut my losses. I don’t know how I’m going to keep up with him in the future, but I hope to somehow. Like I said, he was never the smarter choice, he’s the weirder choice: he’s a big weirdo who decided to make comedy that appeals to weirdos. And having grown up with his writing on Saturday Night Live and on The Simpsons, his shows on NBC and TBS, clips on YouTube, his specials, and his podcast, in a very real sense he has probably been very influential in shaping the weirdo I have become.

This is probably the same for many of you weirdos. This is a space to discuss Conan O’Brien: the man, the career, the ups and downs, the comedy, and the influence on your life. And the hair; we probably shouldn’t forget the hair.