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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
I will always cherish this piece because it records the transformation of Conan from prepared comedian to motivated actor in a few short minutes.
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.
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.
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.
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.
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.
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.
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.
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.
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 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.
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.
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.
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.
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.
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.
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.
This is going to sound immodest, but there isn’t a relationship like and my relationship in a lot of the other shows.
I will say ours is the funniest late-night show that’s ever been on.
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 , silly characters, and presentations that allowed us to sneak in absurdist humor.
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.
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 , which makes me sound like the dumbest producer in television history now.
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.
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.
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.
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 have hundreds of favorite bits from Late Night, but for now I’ll mention just one: The Kayak Guy, a.k.a.
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.
That’s what I loved most about working on the show.