late night

The Show That Made Things Up

Conan O’Brien’s writers — and longtime sidekick — on their favorite memories from the show.

Andy Richter and Conan O’Brien’s “Desk Drive” bit on Late Night With Conan O’Brien. Photo: Team CoCo/Youtube
Andy Richter and Conan O’Brien’s “Desk Drive” bit on Late Night With Conan O’Brien. Photo: Team CoCo/Youtube

Note: A version of this article was first published on September 13, 2018. It has been updated.

In 1993, Conan O’Brien was about to start a new job. He had been working as a successful writer, jumping from The Harvard Lampoon to Saturday Night Live to the hottest show on TV, The Simpsons. But now, through a circuitous route, the unknown (to the public, anyway) O’Brien was about to take the reins of Late Night from David Letterman. And America responded, “Who?

In 2021, O’Brien has been a talk-show host, a theatrical documentary subject, a tour headliner, a superhero, a Funko Pop! figurine, and, most recently, a podcast vanguardist. He’s ubiquitous, and like his idol Johnny Carson before him, somewhere along the way he graduated to the elder statesman of late-night television.

After three time slots, two networks, and nearly 28 years on the air, this week O’Brien will end his late-night talk show and reinvent once again on HBO Max. To celebrate this monumental run, Vulture spoke with 16 of O’Brien’s present and former writers (and one writer-sidekick) and asked them to reflect on their favorite moments and what made O’Brien’s show special.

Tommy Blacha

Writer (Late Night), 1993–99

My favorite all-time bit was “Satellite TV.” Usually it was on a Friday, and you had all week to produce around ten channels. You had a whole staff of talented writers that would pitch wonderfully smart or amazingly stupid channels. Often the pitch process was this quick: “How about a potato that is a judge?” “Potato Judge?” “Yeah. Do it!”

It certainly was a big, pressure-filled workload at times, but it was a rare treat working on that show for me. Producing TV can often be an overthought, grueling, soul-sucking, bureaucratic process. Late Night would often have a visceral feel that made you feel part of this lineage of shows like Ernie Kovacs, Steve Allen, Jack Benny, and Letterman.

It was rumored that Richard Nixon once commented on the show, calling it “madcap.” I don’t know why, but that made me happy.

Andy Blitz

Writer (Late Night), 1999–2006

I loved doing the remotes. I brought my desktop computer to India to find the NBC help-desk woman Sharon, who had been trying to help me over the phone. Another time, I hailed taxis in midtown, trying to find one to take me to Toronto, and finally found a cabbie named Happy who was up for the drive. There’s another where Conan takes me apartment hunting/becomes a dictator and we annoy everyone.

It showed how an extremely ridiculous decision could get approved as long as it was funny. NBC effectively and inexplicably agreed to cover a vacation to India for me and my girlfriend and a crew as long as I came back with good TV. India is a beautiful country filled with people who are kind, hospitable, and great at playing along with insanity. Dan Goor came along to produce the piece with me. He went on to have much more success with Brooklyn Nine-Nine than he did avoiding diarrhea on that trip.

I took a short leave from the show to be in a sitcom pilot and was rudely introduced to the massive amount of useless interference in a show the network is paying attention to. I was ecstatic to return to Rockefeller Center and a show NBC (except for Rick Ludwin) had forgotten they make. The only people standing guard between a stupid idea like the Slipnutz and 2 million people were the two funniest humans on the planet, Conan and [head writer] Mike Sweeney.

Well, also a studio audience very capable of sitting in confused silence.

Glenn Boozan

Writer (Conan), 2019–21

This was a really recent one, but Jesus, it made me laugh so hard: Skyler Higley wrote this bit where he pitched himself as the replacement for the hot guy in Bridgerton. I don’t even watch Bridgerton. “I’m mature enough to work around boobies” — I mean, that just kills me. A dumb character dripping with unearned confidence really hits my comedy sweet spot. Also, there have been so many challenges making comedy (a) over Zoom and (b) with no audience, so to be this funny even with those impediments is a testament to the writing and performing.

Getting to write for this show was a writer’s dream because nothing’s too dark, nothing’s too stupid, as long as it makes us laugh. Everything was funny first. Also, the other writers are all incredibly kind and supportive, which was tough for me to get used to because I’m a raging bitch.

Kevin Dorff

Writer (Late Night, The Tonight Show), 2000–10

My favorite piece from my time writing for Conan is certainly the field trip Conan took to Old Bethpage, New York, to interview the men and women dedicated to the historical preservation of 19th-century baseball. The whole piece was sparked by our excellent stage manager, Steve Hollander, an avid baseball fan. Steve showed me a newspaper article about an “olde tyme” baseball league, and he and I chatted about how neat it all looked — amateur ballplayers in period uniforms playing by 1864 game rules. I took the article directly to Mike Sweeney, and Sweeney took it in to Conan. I think in less than an hour, the remote was approved.

When we got to Bethpage and started rolling, Conan dutifully dug in with the players and the umpire, asking them why they were so committed to this kind of silly project. His tone was gently mocking — pretty much just being a wiseass, nothing too major. Then Conan noticed that there were actual spectators at the game. They were interns from the Restoration, dressed in period costume, and, importantly, they were mostly young women. One of them went by the name Nell. She was shy and rather intense, according to the other interns. She affected a slight Irish lilt, and she’d done her makeup to make her look consumptive. Her companions literally did not know her real name. Conan’s laser beam was activated right then and there. It was a joy to watch them together. Conan asked Nell if she was married. When she said her husband was away fighting in the Civil War, Conan immediately suggested that they should have sex behind his back. When she refused, Conan casually wondered aloud if her husband might already be dead.

The next shot is a reveal of Conan, in full uniform, and in character as an egotistical, hectoring, obnoxious 1864 jock asshole, determined to bang a terminally ill widow. He took turns batting and pitching, terribly, all the while berating his teammates in mostly his own invented 1860s slang. It sounded like a coked-up Teddy Roosevelt channeling a drunk Bobby Knight. In an amazing stroke of luck, Conan’s tirade was suddenly interrupted by a low-flying jet overhead. The flying anachronism terrorized him, and he ran off the field, shrieking. The last shot of the piece has Conan and Nell walking down a country path. As he reaches over to cuddle her, she bats his hand away. Then there’s a lovely dissolve to a formal daguerreotype of Conan with his team, the Wabash Mashers.

In the edit, I added Flatt & Scruggs’s “Foggy Mountain Breakdown,” which was replaced in reruns with less expensive music. But that manic hillbilly energy was just perfect — it sounds so zany and absurd until you realize just how much darn technique it takes to pull it off. That’s true of Conan, too; under every bit of his “jackassery” (as he calls it) is homework. Lots of homework. Late one night, we showed Conan the final cut. [He said], “It’s like Field of Dreams meets the Donner Party.” I was too tired at the moment to understand what a high compliment that was. Conan wanted it to be the last piece on his last Late Night episode. He said he wanted it played at his funeral.

I will always cherish this piece because it records the transformation of Conan from prepared comedian to motivated actor in a few short minutes. At the very moment Conan the comedian acquires his target — in this case, the lovely Nell — Conan the performer takes the wheel, now fully armed with a genuine feeling: I’m gonna play me some baseball and get me that girl.

Andrés du Bouchet

Writer (Late Night, The Tonight Show, Conan), 2008-21

I was lucky enough to play a lot of different silly (loud) characters on the show, but my favorite would have to be Leslie, the guy who dresses like a Game of Thrones character but is actually obsessed with the show Wahlburgers. I wrote several installments of this bit, all of them involving me in the audience absolutely screaming at the top of my lungs, and they were all a blast. Oddly, I can’t find my favorite version online, in which I got to introduce another character named Mark Wahlb. Sensing the audience’s anticipation that Mark Wahlberg was about to walk out onstage and then stopping on a dime after “Waaaaahlb” and sensing them deflate as yet another dumb character walked out … Yeah, that could be my single favorite moment in over a decade of working at Conan.

I’m obviously biased, but I think what sets Conan apart from other late-night shows is Conan. He’s not just the star of the show, but he’s ironically also the show’s secret weapon — not just a presenter-interviewer but a legitimate comedian and sketch writer-performer in his own right. He is constantly shifting between being the ringmaster of a bonkers comedy circus and being the clown that is causing the chaos.

Jessie Gaskell

Writer (Conan), 2014–21

I doubt anyone will mention anything from the past year because it’s been so hard, emotionally and logistically, to create comedy during this time. But we stayed on the air with bare-bones production throughout the entire pandemic, and I hope we’ll look back and be proud that we kept producing comedy under duress. One of my favorite things we did last year was pitched by writer Skyler Higley: a Christmas special in September, “in case we don’t make it to Christmas.” It was dark but also really joyful. When the election got especially stressful last year, I created a bit where Conan delivers monologue jokes and is rewarded with a voice-over (Dan Cronin) singing to the St. Elmo’s Fire theme, and each verse is hyperbolic praise for how Conan is changing the world with his comedy. It’s extremely tongue in cheek, and we used a leaf blower on Conan’s long, weird pandemic hair, and it still makes me smile.

Jon Glaser

Writer (Late Night), 1998–2008

“Satellite TV” was always fun to write. It was completely open-ended to whatever short, weird, random, stupid idea you could think of. [Late Night] obviously catered to a specific, weirder sensibility, and it was fun to work with a group of people who shared that sensibility. And having to write that type of show on a daily basis allowed for a wide variety of extreme stupidity to make it onto TV. It was a very fun job.

Laurie Kilmartin

Writer (Conan), 2010–21

[Picking a favorite bit] is an impossible question to answer, but I love Brian Stack’s Joe Galliano character, who was responding to charges that his brother, designer John Galliano, is an anti-Semite. It’s Stack doing an insane character without breaking, it’s Conan trying to break him, it’s costume changes in front of a live audience, it ends with Stack crossing in front of Conan — what more could one want?

To me, what was really astonishing is that Conan remained silly and stupid even in the Trump years. That entire presidential term was like a four-year-long state of emergency, and I think the obligation to respond to it became an anchor around many comedy necks. No matter how many times Trump was “destroyed,” he remained. Conan decided not to enter that fray, and that was a relief to us writers. Most of the comedy on our show was meant to take you away from all that, not remind you of it.

Todd Levin

Writer (Late Night, The Tonight Show, Conan), 2009–21

I think the writers at Conan — some of whom were writers at Late Night — always had a little chip on their shoulders because the TBS show was never really part of the conversation when talking about Conan. It makes sense, because I think Late Night casts such a long shadow. But we’ve been putting together clips packages for this show’s final weeks, and I was sincerely surprised by how many weird, funny things we were able to do on a network most people aren’t even aware is part of their basic cable package.

There were a lot of recurring bits I looked forward to watching, but my favorite thing to write was always WikiBear. It was based on a real toy I’d heard about that could search the internet, and I wrote the sketches with Brian Stack, who also voiced the bear. Stack is a brilliant performer and so much fun to write with, because he’s this objectively sweet, soft-spoken person who also has a seemingly limitless appetite for the horrific. So our brainstorming for this sketch usually started with each of us just half-remembering the most disturbing things we could think of, like the wreck of the USS Indianapolis or the candiru fish, and then gleefully Googling them for details.

WikiBear stands out to me for a couple of reasons. First, it was a coup just getting him on the show so often, because it meant Conan had to spend five to six minutes of airtime playing straight man to a dead-eyed children’s toy. Also, because WikiBear was so disarmingly cute, the audience was never really bummed out by him, even as he was heaping accolades on the Zodiac Killer or telling kids in the audience, “Never trust a cop!”

I think what sets Conan apart from the other late-night shows is that he always provided a home to silly, often conceptual comedy, even until the bitter end. In a lot of ways, the thing that defined late night for so long — absurd sketch comedy — has actually become sort of out of fashion because “virality” has become so essential to a late-night show’s survival. So things like games with celebrities, parodies of well-established pop culture, and, more recently, these more polemical segments that have served as a kind of cultural statin for the nation’s collective hypertension under the Trump administration have become more common in late night than, say, a sketch where Conan talks to a teddy bear about the Heaven’s Gate cult. And I’m really glad there’s so much variety in late night now, but as a writer and a huge fan of sketch comedy, I definitely appreciate that Conan always remained a comedy purist. Even if our tent is smaller, at least everyone in the tent is laughing.

Brian McCann

Writer, performer (Late Night, The Tonight Show, Conan), 1995–2012

I always thought Late Night was at its best when we got to present insane ideas, and I think the bit that allowed that the most was “Satellite TV” — Conan and Andy [Richter] flipping through channels to see what’s on and finding stuff like a channel called Babies Reminiscing, where there is sappy music playing over a montage of babies looking out over lakes and parks. Or the What Hurts More? channel, where Matt Walsh just whipped objects at me and I shouted out which one hurt more. “Satellite TV” allowed for a fast-paced dose of crazy, and the stuff we shot had really good production value.

The way Conan embraced the absurd was so refreshing. Other shows tried to go that way, and it didn’t feel authentic. I had the most fun when the whole staff was urged to bring their own voice to whatever they were doing. Most shows I’ve worked on have a single voice and single point of view, which greatly narrows the type of comedy that can be done successfully.

Matt O’Brien

Writer, head writer (Late Night, The Tonight Show, Conan), 2008–15; 2015–21

Early in the TBS show, I wrote a sketch about the founder of the network, Ted Turner, stopping by to berate Conan. Conan wanted him written as a firebrand coot, even though Ted Turner isn’t exactly like that, and we were very lucky that Will Forte agreed to play him. I had seen Will do an insane Zell Miller impression on SNL and thought that same energy would work for an insane Ted Turner — and wow, did he deliver. The only thing I knew about Ted Turner is he’s obsessed with buffalo, so we rented an aluminum buffalo statue for Will to ride out onstage, and it was just pushed out on the platform by a crouching stagehand. It was as low-rent as you can imagine but somehow worked. Whenever the show traveled to different cities, our Ted Turner would usually make an appearance, and some poor person had to drive a lifeless aluminum buffalo across the country so that Will could scream at Conan. A complete waste of resources and time, which also might describe our show.

Someone described our show as the intersection of smart and stupid. I’m not sure anyone in history has existed in that space more brilliantly than Conan. Also, the breadth of remote segments he’s done is unmatched. You can put him in almost any situation and he will find the funny off the top of his head, and he still has to pay us for “writing” it.

Andy Richter

Sidekick, writer (Late Night, The Tonight Show, Conan), 1993–2000; 2009–21

My favorite bit was something we used to do called “Satellite TV,” and the setup was: We have this big satellite dish here at Rockefeller Center, and we have dozens of channels that you can’t get elsewhere. Like Lincoln Money Shot Channel and things like that. And then there were just slo-mo shots of Lincoln having orgasms. So that was just a chance to be absurd — a chance to just give you pure laughs that are not connected to anything.

Our bits weren’t going to come out and make you love them. They were weird! And they were right there in front of you, and you could come to them and love them, but we’re not going to come to you and say, “We understand that maybe you have a tamer sensibility than the people writing this.” We were like, “Hey! This is what we do. This is what we think is funny. And you’re welcome to come onboard, but it’s all we can do — we can’t cater to you.” And luckily, there were just enough young people who got it and liked what we did. Also, we got so many talented people. Amy Poehler, Andy Daly, Matt Walsh, Rob Corddry, and Rob Huebel I think did a bunch of bits for us — just tons of people that went on to be very successful comedians, and we got to utilize their talents really early on.

We used to kill ourselves. I remember within the first couple years, when I would go off on the weekends and do remotes, there was one stretch of 27 days where I just worked straight through. We were doing the show five days a week, I was going away on weekends, then I would come back with the remote and it was up to me to edit it most of the time. As time went on, that changed. But there’s plenty of times I was there until two o’clock in the morning editing a bit, but we just felt like we had to do it. We just kind of poured ourselves into the show, and that’s just not sustainable — not just for your life, but the show would just stop being funny if everyone’s fucking miserable. Like that “Desk Drive” bit that we used to do? That was a fucking nightmare every day. It would put everyone in a bad mood because it was just so complicated: the tape rolls, the green screen, just getting everything right. It eventually slowed down. We would just do less complicated bits. We still get away with it, I guess; it’s hard as you get older to be as weird. It just is.

This is going to sound immodest, but there isn’t a relationship like [Conan’s] and my relationship in a lot of the other shows. Even Ed McMahon was a bit of a prop; he was an object, rather than a character, in many ways. In fact, a lot of the old-timers, when we first came on, thought I was the guy where you could go, “And this fat dum-dum over here …” And then they’d quickly learn that the audience would go, “Now, don’t do that! That’s our guy.”

I think our brand of humor has always been true to itself. Our first concern wasn’t what’s going to work; it was what’s funniest. Those are two different things. There was a standard of how funny something had to be. I will say ours is the funniest late-night show that’s ever been on. And I loved Late Night With David Letterman. That’s the only one that even comes close to us.

Robert Smigel

Head writer, producer (Late Night), 1993–95; occasional writer, performer, 1995–2021

I was head writer-producer when we started, never wanted a job more, and had some very clear opinions of what would make the show exciting and original. Conan and I both loved high-concept, nonsensical stuff, but Letterman had brilliantly cornered the market on a lot of that on his Late Night. We had just come from Saturday Night Live, and I wanted to bring sketch comedy to a talk-show format, which hadn’t been done since Steve Allen’s version of Tonight in the ’50s (I got to tell Steve Allen once that we stole the half of his show that Letterman didn’t steal). So we did a lot of celebrity interviews (in our own abstract, cartoony form with “Clutch Cargo”), silly characters, and presentations that allowed us to sneak in absurdist humor. We used to say we reacted to Letterman’s penchant for “found humor” by being “the show that makes things up.”

A perfect example was the sketch that led to Triumph. Letterman was getting laughs on the Late Show by having Westminster dogs run down the aisles of the Ed Sullivan Theater. That was it, but it was funny. So I thought we should present Westminster dogs, using these realistic dog puppets my wife had just bought for me, and have the dogs display various ridiculous talents: dogs playing dueling banjos, a magic act, a Jack Nicholson impersonator who put his paw over his forehead to do Jack like every hack comic did back in the day. I didn’t suggest “insult-comic dog” until about four years into the bit, long after I’d left the head-writer job.

We set down plenty of restrictions early on that helped us separate ourselves from Dave and establish our own style, including no comedy using stagehands and, believe it or not, no remote segments with Conan (unless they were scripted sketches), which makes me sound like the dumbest producer in television history now. But it helped force us to come up with lots of original looks and concepts, like Conan’s idea to “drive his desk” in front of a green screen. And within a year, we started sneaking in some less structured remotes with Conan, and, of course, they — and Conan himself — became the best part of the show.

Getting that show off the ground was both the best and toughest experience I’ve had on television. We took a lot of crap around the studio for doing so many complicated sketches that took a lot of time and work, cost money, and all for a completely unproven, unpolished performer. Only the writers knew how funny he was back then. I remember hearing some staff grumbling that “it’s like we’re doing Every Night Live.” Years later, I visited the Fallon show in its early stages, and now they were doing even more elaborate sketches than we were, only with a host that everyone knew well and had full confidence in. And I actually heard a staffer saying, “We love it! It’s like we’re doing Every Night Live!”

Andrew Secunda

Writer (Late Night), 2001–3

As the often-mocked biggest nerd on staff, I had proposed a remote where Conan hangs with the fans waiting endlessly in line for Star Wars: Attack of the Clones. When I heard it had become a Triumph sketch, I was a little intimidated. Robert Smigel, Triumph’s creator and voice, though universally and justifiably considered a comic genius and legend, had a huge reputation as a difficult perfectionist. I was concerned that in having Triumph mock the nerds in line, we’d be picking on the defenseless, but as soon as we started, it was clear they loved it.

Smigel gets in such an intense, focused zone when he’s Triumph that I kind of hung back, but when a giant Darth Vader cosplayer lumbered up to Triumph flanked by two stormtroopers, I whispered to Smigel that he should ask “Vader” about his chest-plate, then ask, “Which of these buttons calls your parents to come pick you up?” Smigel didn’t hear me and said impatiently, “WHAT?” I was gonna bail, but I repeated it, and now one of my proudest comedy moments is on film, as you can hear Smigel still laughing as he turns to nail the joke as Triumph. I only take credit now because Smigel has publicly credited me with it several times, which is generally unheard of.

After Smigel crafted the remote down in the edit, we ran it for the previous night’s studio audience, and in an act of great generosity, Smigel grabbed me and we sat in the guests’ chairs on set next to Conan’s desk as they watched the remote. I’ve been onstage as an improviser thousands of times, but sitting in those chairs, I’d never experienced the explosion of laughter blasting at me from an audience like their reaction to Triumph making fun of those delighted geeks.

Brian Stack

Writer, performer (Late Night, The Tonight Show, Conan), 1997–2015

There were so many Late Night characters I loved — some very famous, like Triumph the Insult Comic Dog; some just silly one-offs, like Jabba the Foxworthy (Jabba the Hutt with a Jeff Foxworthy–like mustache and joke delivery). I’ll always be very grateful that I got to do a few recurring characters myself — like Hannigan the Traveling Salesman, the Interrupter, Frankenstein, and Artie Kendall the Ghost Crooner — but I’ll always have a very special place in my heart for Andy’s Little Sister, Stacy, a 13-year-old girl with pigtails and orthodontic headgear (played by the brilliant Amy Poehler) who had a huge crush on Conan.

It was the first character sketch I ever wrote at Late Night, and Amy’s brilliant performance made my very simple sketch idea 100 percent better. I’ll always be grateful to her for that. I was originally going to cast a real 13-year-old girl as Stacy, but Amy managed to actually look 13 while giving a full-on powerhouse performance. She can do anything, though, obviously.

Mike Sweeney

Writer, head writer (Late Night, The Tonight Show, Conan), 1995–2021

I have hundreds of favorite bits from Late Night, but for now I’ll mention just one: The Kayak Guy, a.k.a. the There’s No Reason to Live Guy, has a warm place in my heart because (a) it was born out of desperation as we sat in the writers’ room at 10 p.m., still needing a second sketch for the next day’s show; (b) it was pitched and performed by the always brilliant Brian McCann; (c) it contained the hidden drama of McCann having to stick two entrances by running off-camera down two hallways and a long flight of stairs; and, most important, (d) it was an instant hit with the audience, allowing us to bring it back a dozen times and thereby avoid a dozen more desperate meetings at 10 p.m.

Andrew Weinberg

Writer (Late Night, The Tonight Show), 2000-10

Overall, I’m most proud of the aggressively stupid things we did. “Cactus Chef Playing ‘We Didn’t Start the Fire’ on the Flute” comes to mind. It was exactly what it sounds like: a cactus wearing a chef’s hat, holding a flute with its branch-arms, while a flute-only version of the Billy Joel song played. It wasn’t clever or smart. There was no deeper meaning to it. It really had no reason to exist at all. But it did, because we all agreed it was somehow funny.

That’s what I loved most about working on the show. The image of a cactus wearing a chef’s hat popped into my head, and two days later, the General Electric corporation paid people to build it and broadcast it on network television.

The Show That Made Things Up