On Thursday night, Conan O’Brien hosted what he has said would be his final late-night television episode, on his last late-night television program. He began on TV as a largely unknown 30-year-old in 1993 with exactly the kind of pedigree you would’ve expected then: Harvard-taught, an alumnus of both The Simpsons and Saturday Night Live, an advocate for the weird and disruptive trends emerging in comedy to which, despite him being an Irish-Catholic Massachusetts native, he had a singular pulse.
My introduction to Conan’s work was via Late Night With Conan O’Brien, the show he hosted as the wedge between his beloved Johnny Carson and Jay Leno and which was repurposed as a day-after lead-in to The Daily Show on Comedy Central for a while. When it came time for Conan to assume his seat at the top of NBC’s hierarchy, it suffered from poor ratings and a shift back to late-night along with the Tonight Show name, which Conan would fundamentally not accept. A back-and-forth ensued, and Conan eventually ceded the seat, leaving us bereft of him for a time while he popped up on tour and at music festivals – more on that later.
I understand that his is mainly a slightly-older generation of an audience, the tweeners that both lived to experience Nevermind in real time, cognizant of it or not, and also know how to navigate social media without sparking fights at a dinner table, but my friends and I – white and well-off-ish enough as we were – liked Conan better than any of the others mostly because we never knew what to expect.
Below is a list, mostly off the top of my head, of my personal favorite Conan segments, recurring and otherwise. I know this isn’t the end, but HBOMax’s app is horrendous, and anyway, it isn’t as widely accessible as he has been for thirty years otherwise. Conan, we only wish you well, as you ever wished us.
- Coked-Up Werewolf: The epitome of Conan’s random character creation and interruptive skill, Coked-Up Werewolf didn’t really have to *do* anything in order to be noticed. An example sketch involves him handing Conan a paper outlining the following weeks’ guests, excitedly and variously gesturing toward the camera, and then promptly falling asleep. Relatedly, I’ve never done cocaine.
- Triumph at Star Wars: Attack of the Clones: As much as I loved (and still love) dogs growing up, I never had much affinity for Triumph, the creation of SNL animated/weird segment aficionado Robert Smigel. But having Triumph, a Smigel-wielded hand-puppet, show up to insult quote-unquote-nerds at a movie premier and attack the particulars of their outfits was lightheartedly incredible television. His (and Smigel’s) dress down of the full-on Darth Vader that appeared is especially sublime.
- Paul Rudd, Mac and Me: It began anomalous and became expected, somehow; it could only have been the product of a show that Conan was hosting and on which Paul Rudd, of all people, was a regular guest. Sometimes going out of his way to join whatever iteration of the show Conan was hosting, Rudd would roll in, ageless and handsome as ever, ostensibly to drum up support for anything he might even be minimally attached to, only to introduce a clip from “that” and then show this. That audiences came to expect it was immaterial; Conan’s audience’s always expected the weirdest. This recurring bit sits chiefly among them, with Rudd’s Dorian Gray making even compilations of the appearances readily enjoyable.
- “Ginger, no!”: I will make one concession with this list – The Ringer, retrospective hounds that they are, reminded me of this, but once they did, I remembered every detail so vividly that it was like I was once again on the upstairs couch in middle school, trying to place the gun in the dog’s paw on a non-HD TV.
- NYC Transit Strike: I don’t want to bore you with the details, but when I took an on-campus job in college, I updated my current work description on Facebook with the video of Conan rolling around New York City and picking up random people. Some were more hospitable than others, but everyone kind of, sort of understood that we had to get somewhere, and given the transit strike happening at the time, Conan understood that, too. In his own, inimitable way, there he was again: being weird and serviceable in public.
- Max Weinberg: Turning the drummer of Bruce Springsteen’s beloved E-Street Band into an insane and neurotic character was a masterstroke; in at least partial response to David Letterman’s “Yeah, totally” relationship with Paul Schaffer, Conan took Weinberg to improbable heights, staging him in NBC takeoff “The More You Know” segments.
- Old time baseball: An all-time classic among late-night television venture clips, Conan’s entry to a Central Park baseball league that specializes in 1864 base-ball rules eventually sees him don a Civil War-era facial hair and the old timey language at which he somehow specializes like no others of his generation of talk show hosts, despite the rest of them being either older or around his age and extremely (although not quite as) white.
- Will Ferrell as Robert Goulet: This begat Anchorman, sure, but it also begets James Cordon’s carpool karaoke and several other extremely contrived gambits. None of them are better than this. Ferrell’s offhanded non-sequiturs (“How’s the backhand?,” “I’ve CHOKED bigger men than you!” and “It feels good to be back on top”), declaration of where he is (“Burbank?” as an answer and a question) and repetition of his own last name (“Goulet!”) lead into an incongruous Rodgers and Hammerstein lounge act, Conan barely able to maintain order. No matter. Aside from (and not at all excusing) Ferrell’s ill-advised direct quotations of the Notorious B.I.G., which aren’t great in the SNL clip that Conan uses to introduce him. One of my friends and I have been quoting Ferrell’s first appearance as Goulet on the show since at least middle school, and while both of them are much better at it, I am by far much more annoying at it. Conan would appreciate both approaches wholeheartedly. Mmmm, Burbank? Say, Johnny, where’s Ed?
- [Celebrity] Secrets: “You’d think that being a famous rock star, married to a supermodel, would be one of the greatest things in the world. It is.” Specifically, when the segment that called for big names to declare never-before-heard facts or short anecdotes about themselves brought in David Bowie or Jeff Goldblum, it was the comedic equivalent of a blank check direct deposited off-shore. How dare you speak to me?
- Spending NBC’s money at will in the lead up to being re-replaced on The Tonight Show: At the time, Conan’s feud with Jay Leno was the kind of big deal you could passively pay mind. It mattered, but it didn’t, the kind of institution-rattling we probably needed that largely didn’t play out in anyone’s favor – what’s your favorite Leno bit, and why does it only involve his cars after the fact? The Tonight Show’s ratings took a hit with Conan in charge, the public not prepared for his eccentricities to play out an hour earlier than they were used to, and that eventually led to Jimmy Fallon’s current milquetoast schtick, house band and regularly exceptional musical bills notwithstanding. But this became instant must-see television for The Tonight Show, Conan seemingly spending the kind of gratuitous money you couldn’t count that NBC’s advertisers might have been losing in light of the switch. Conan’s never had a problem sticking it to authority, be it Harvard or anyone else, but “Expensive Comedy Bits” begat, of course, the Super Bowl horse and Bugatti Veyron Mouse, set to the Rolling Stones’ master recording of “Satisfaction.” It was the best-ever televised response to getting played: we’re all accountants after something like that.
- The last Tonight Show monologue: The crowd burst into a “CO-NAN!” chant, and then the notes about cynicism resonate always, but particularly today; while Conan maintains a perspective with which I and many others identify roundly, the situation that he’d been through with all of it – the taking his dream job, that job being seized, and his renouncing the dream job – seemed to have taken him to a breaking point. The charges he left NBC with at the end of his run represented someone scorned, a person who had trusted and whose own trust had been broken. Even so, Conan’s resilience in the face of publicly corporate bullshit was noble, a person who had stood up to the largest corporate beast in his game and was hoping to come out at least breaking even. In time, he would.
- Conan visits his Harlem neighbors: “Ummm, I like ABBA” b/w a rumination on Harlem soul food institution Sylvia’s being met with, “IT’S NOT KOSHUH!” Fallon’s too busy chuckling his way through cultural imperialism to be able to pull anything like this off with this brand of candor.
- Jordan Schlansky, in Italy: All of Conan’s late-period interactions with executive producer Jordan Schlansky – including the latter’s explaining what an executive producer actually does – are executed to perfection, Schlansky providing the pretentious straight man foil to Conan’s entire straight man-turned-funny act. Every part of the trip to Schlansky’s cherished Italy, from planning through execution, is great, up to and including Conan’s knowing, affected Italian accentuations on words that do not exist in the native language and purposefully ignorant anti-embrace of the language itself, Schlansky correcting him all the way. Schlansky may be the expert on Italy, but Conan’s rejection of that fact leads us to his own favorite meal: a feast of absurdity.
- The Walker, Texas Ranger lever: I saved this for last strictly because it was my all-time favorite bit that Conan ever did, across any of his shows. It was delightfully stupid, as they all were, born of the merger that created NBC-Universal and, thus, allowed Conan the opportunity to utilize random clips that his then-network now owned. He explained it nearly every time he pulled it, including goading Peter Gallagher into reaching for the prop that didn’t actually do anything, but I would sit there after school in seventh or eighth grade, with nothing better to do than hope that Conan would interrupt himself in order to present an inexplicable fight scene or “Walker told me I have AIDS” clip. What were those writers thinking? Immortality, exclusively, which is evident in the Chuck Norris jokes that simmer among the targeted demographics a generation and a half later, many of whom never saw the show running on repeat during USA’s down hours in the breaking points of any day.
Bill Hader, who may be the funniest person currently on the planet and whose first late-night appearance came on Late Night, said that Conan’s comedy was the first thing he felt was his own, not of his parents’ generation. That I watched The Simpsons with my parents, but not Late Night, makes sense, in that realm. It had just enough in common with what I’d seen in Marx Brothers movies and Warner Brothers revues that it made sense, but it also struck toward the psychedelic white spaces of Willy Wonka’s boat trip and what happens when a basketball lands directly on the back rim. These things are inexplicably funny, and at his best, Conan is, too.
Speaking of which, what has always stuck with me with Conan is his ability to identify a place to leave that space. No one in comedy, a practice as technical as music – Conan well-known as a musician himself – and equally as rhythmic, leaves wide spaces where they need to be as does Conan. The man can manipulate feedback, and play it to his advantage.
Wherever Conan lands, he will do well and good; he expected us not so much to listen, but to watch. Isn’t that what television is? In a changing media era of being able to recall clips instantly and take notes, Conan was the late-night host who knew when things weren’t quite real to you at home, even though he’d play along. It wasn’t cutesy, but it was nice; it wasn’t conceited, but it was smart. What more can any of us hope for out of a life spent peaking, and gracefully moving on to the next, better thing?
 Conan, from here on, for the most part; “O’Brien” as a moniker seems confusing and is also disrespectful of a certain, sometime TwH contributor.
 I don’t and never have worked in television, so I don’t know what these are called. I know them as off-sites, but they aren’t usually televised.
 Hi, Spencer, and I’ve still got Dave’s phone number.
 I went looking for an itemized list of this week’s expenses, even if it wasn’t real. If any reader has that, feel free to DM.
 To the Walker writers, and to the point of the sketch entirely: WHY did this storyline exist?
 God’s Plan: When I first tried to copy-and-paste this into the TwH CMS, I was met with an earlier copied clip of Walker, Texas Ranger. It can happen at any time to you, too.