FYI, this isn’t just a list, it’s an argument laid out in multiple parts that are trying to prove the point that Conan O’Brien is the greatest late-night host of all time. Someone who directly or indirectly influenced more than two generations of comedy writers, comics, actors, and nerds. To be sure, there are originators and other trailblazers worthy of serious consideration — the Carsons, Lettermans, Stewarts — but Conan and his merry gang have gone further, bigger, and bolder, setting a tone that shows it’s okay to stray from classic formats and the idea of what late-night comedy is supposed to be (both on-screen and as a business).
I may be way off base with this theory. I may be biased since I grew up watching Late Night, following from day one. Before you decide if there’s validity to this claim, I’d love for you to weigh the evidence while also basking in the amazing moments and genius characters that have defined these shows.
Some caveats: These moments and characters (and elements) are pulled from Late Night, The Tonight Show, and Conan. I’m trying not to double up on characters, which is why there’s only one Triumph sketch. Also, I brought in ringers. While they are not explicitly co-signing my claim about Conan’s number 1 all-time status (I didn’t ask), we have compiled a few anecdotes and quotes from former Conan guests, comics, and writers that will be sprinkled in here and there.
Now, let’s begin with the 25 best characters, moments, and elements from Conan’s 28-year run. Please know the pain it is causing me to know I’m surely forgetting things and the angst I have over leaving off things like the Year 2000, Conan’s trips to Ireland and South Korea, Clueless Gamer, The World’s Fastest Menorah, and the American Girls Doll Museum, as well as characters like Preparation H. Raymond, and Pimp Bot 5000. I am so sorry, Pimp Bot 5000.
25. The Extensive Cast
Conan’s writers were perpetually in the mix for on-screen time and many of them are going to get more specific call-outs below. More also needs to be said about the brief merge of the Upright Citizen’s Brigade into Late Night, and actors like Abe Vigoda, Nipsey Russell, and Mr. T. But we’d be remiss if we didn’t point out the other behind-the-scenes players that helped build the franchise without any on-camera experience or aspiration. People like announcer Joel Goddard, bandleader Max Weinberg, graphic designer Pierre Bernard, Conan’s assistant Sona, associate producer Jordan Schlansky, and prop master Bill Tull.
I interviewed Tull once and when I asked him about a specific sketch where they put ET in a wood chipper, he said, “we put a lot of things in the wood chipper in those days.” It remains the greatest sentence anyone has ever said to me.
24. Conan Gives His Staff Their Reviews
As stated before, Conan has a long history of pulling his staff into the show, and this bit, which follows other peeks into the office culture behind the show, is demonstrates the funny that can be found when Conan lovingly antagonizes the people he works with.
From Mo Mandel, comic and past guest:
“It just showcases how effortlessly likable Conan is because he’s just berating these poor people and being so mean but you totally love him and are on his side the whole time and know he’s in on the joke even though he’s playing it straight. That only comes from a person who is super nice in real life, so much so that even when they play angry you can tell they’re a sweetheart. People always talk about the self-deprecating Conan but he plays an equally good villain.”
23. The Impact On Stand-Up And Comedy
Johnny Carson’s Tonight Show stood out as the place where comedians met America in his era, and Conan took the mantle, focusing on the burgeoning alt-comedy scene of the ’90s doling out time to the likes of Marc Maron, Sarah Silverman, and others. As time went on, that continued with a new batch of comics in the 2000s and 2010s (Mike Birbiglia, Taylor Tomlinson, Mo Mandel), further establishing Conan as a sort of Godfather for comics. Which is to say nothing of the influence he has had on comedy culture, in general. Here’s Mike Birbiglia — comic, former guest, and former Late Night intern — had to say something about that.
“The first time I was on the show, I was so nervous because the people who make the show were sort of like my older brothers or sisters or something. My sensibility was raised watching hundreds of hours of the show. And then Conan, Andy, the writers, and the producers have been nothing but absurdly nice and generous. And I feel very lucky to have learned what I learned from watching that show and watching people work behind the scenes on the show and then to have been lucky enough to be a guest on the show. Conan and Andy are just two people who I admire most in this whole insane field of comedy. When Bill Hader came on my podcast, we talked about how influential that show has been to an entire generation of comedians.”
22. The Late Night Debut and The Tonight Show Finale
Both of these full episodes showcase the defiance that Conan brought to the mix at very different moments in his career when various “experts” were already counting him out. In the first episode — a wall-to-wall cavalcade of wild ideas and comic weirdness that we once dubbed “punk comedy art” — O’Brien leaned into the crushing expectations of his new post and the resulting anxiety, creating one of late-night comedy’s singular hours of television.
As for The Tonight Show, O’Brien stayed on the air through the slow-rolling PR nightmare that was NBC’s horrific handling of the show’s hand-off from the Jay Leno disingenuous in denim experience to Conan and company. And he did it with class, fire, and irreverence, supposedly making NBC pay for ultra-expensive comedy bits (the Bugatti Veyron mouse and its Rolling Stones theme song!) as a means of attaining some hilarious revenge. At the close of his final episode, O’Brien played “Free Bird” with an in-costume Will Ferrell (and his very pregnant wife, Viveca Paulin, who gave birth hours later) after delivering a farewell address that pushed back on the notion of cynicism and showed us all, one more time, what a gaggle of schmucks NBC was.
21. Artie Kendall
A ghost who used to croon in Conan’s Late Night studio back during the depression played by writer Brian Stack, Kendall warbles on about being in a Russian brothel getting high on Thanksgiving and bashing in the heads of the unemployed (“crackedy skull!”). Truly, Late Night was ahead of its time in reminding us that the things our grandparents watched and listened to were utterly terrifying and often super sexist and/or racist.
20. The Slipnuts Open For Slipknot
There were probably 18,000 fans at that arena utterly confused by what they were watching. Maybe even pissed when a weird comedy trio came out to open for heavy metal giants, Slipknot. But there were probably 100 people who found out who the Slipnuts were and the point of the bit, and to them, it probably became the greatest thing they’d ever seen. Gone in an instant for everyone else, imprinted for a lifetime on those select few. The power of aiming for the passionate niche over more casual and fickle broad acceptance. The power of not being afraid of confusing the masses to find the ones who get it. Another Conanverse staple.
19. Conan Plays In The Snow
Similar to the Andy Blitz goes to Toronto moment, this “fishing expedition,” as show writer Michael Koman calls it, demonstrates the recipe for success for so many key bits. Go someplace (maybe a snowy street or to Cuba) with a microphone and the flexibility to go with whatever and whoever you find with Conan leaning on his amazing improv skills to create something genius, random, and real. In this case, the Blizzard of 2003 provides the setting, with Conan goofing off in the snow, climbing massive mounds, and discovering pure gold in the form of a very shouty old man (who would pop back up on the show a few more times).
18. Andy Blitz Takes A Taxi To Toronto
Conan going apartment hunting with Andy Blitz should be on this list, but I can’t not put this utterly genius concept where Blitz (a longtime writer on the show) takes a cab to Toronto. Ever take a really long Uber ride? Like really long? Imagine going 12 hours with an overnight stop.
“You wanna pull over and do trust falls?” It’s amazing the awkwardness and resulting comedy that comes from two strangers put into close proximity with each other. Nothing is forced, it’s just gentle weirdness and a flash field trip.
17. Late Night Goes Claymation
The show had dabbled with claymation before (a Christmas special, a Passover special — both as shortish bits), but in 2003 they repurposed a whole episode, spending untold amounts of money and months of production to create a truly imaginative and fun visual experience. The ambition of the show and the “why not?” attitude of the people making it is truly startling when you compare what they’ve done to, really, any other show. That’s no disrespect to Letterman (the only real competition in my opinion) and, in particular, his own version of Late Night which, of course, preceded Conan’s and plowed the field where all these experiments got their start (I’ll note Letterman also used to add neat touches to freshen up reruns). But it has to be said that the scale and commitment to big ideas outpaced even Letterman’s in his show’s prime (in a very different time with different technical capabilities and budgets).
16. The Rockefeller Center Fire Special
The Rockefeller Center Fire episode makes it on this list not just for the show’s willingness to change things up and record outside (with Sam Jackson in a Brookstone massage chair), but for its ability to do that so completely and in an instant when their studio was damaged by a fire. Sure, desperation plays a part, but there’s a supernatural level of confidence at play as well. As close as they got to being canceled in the early going while, at the same time, pursuing a kind of budget bin avant-gardism, the show survived. Maybe it’s a thing where, after a bunch of near-death experiences, they began to believe they were immortal and, thus, could do anything.
14. Christmas Shopping Desk Drive
There’s an innocence to the general concept of Conan and friends being able to go anywhere they can imagine thanks to a magical desk (and green screen tech). Like it feels fit for a kids show and you can’t help but grin and embrace the silliness of it. Vehicular manslaughter and Tickle Me Elmo theft be damned. But besides that, this is also the best example (alongside the Clutch Cargo sketches from the ’90s) of the inventive lo-fi ways the show used to make their budget work while still standing out and leaning on, in particular, the talents of Conan, Andy,and Smigel.
13. Interviews
There are far too many that should be on this list but Jennifer Garner and Conan warring over the word “snuck,” Mel Brooks paying tribute to Sid Caesar, and all the raucous and familiar chats with friends like Timothy Olyphant, Will Ferrell, Lisa Kudrow, Aubrey Plaza, Martin Short, and the always-in costume Adam Pally all come to mind as standouts.
Conan didn’t jump into the show as a natural interviewer, but he evolved quickly to find comfort and gain master status. His previous digital series Serious Jibber-Jabber and his podcast, Conan O’Brien Needs a Friend, all free him to have longer, more multifaceted conversations now, joining with the late era of Conan with its longer interviews to prove that he’s now become pop culture’s ultimate defender for the value of a good conversation. Here’s hoping that remains either with the podcast, HBO Max series, or otherwise.
From Joel McHale, a frequent guest:
“He would be just as thoughtful talking to Obama as he would a kid on the street. The first few times I went on, I had to really control myself because I’m such a big fan. I get giddy when I’m on his show. And the last time I was on, they just aired the whole 25 minutes. That’s really how we talk to each other. It’s a heightened version because we’re on camera and we’re slinging jokes, but our wives just roll their eyes at each other when we’re talking. I don’t know how to describe it other than he’s a lovely genius.”
13. DInner With Conan And Jordan
Conan and Jordan Schlansky are like the Odd Couple re-born, with Conan flummoxed and Jordan barely tolerating the incessant picking at his very specific way of being. And it’s never better than when they take their act on the road, specifically when Conan went with Jordan to the restaurant in Italy where he was a supposed big deal and when Conan took Jordan to an Olive Garden to more or less mock him, burning his nipples with a hot breadstick in the process. I don’t think they’re taking suggestions, but I’ll go ahead and say that at least part of the new show needs to be Conan and Jordan recreating Steve Coogan and Rob Brydon’s The Trip franchise.
12. Andy In The Wild
For a time in the early days of the show’s run, Andy Richter was a primary force with remotes for the show, going out to Woodstock, the NBA Finals, the Tonys and other places. And it’s all great. Richter has an approachability to him that masks his killer comedy instincts. He’s like a cherub with a pistol taped to his back. I’m using a couple of examples here. One is a trip working the press line at the VMA’s where he sells a sad-sack routine trying to sell his music videos. And then the bomb drops and we’re seeing an amazing recreation of Eddie Murphy’s “Party All The Time” video. Then there’s this one in a dive bar where he mines laughs in what could only be described as a depressive rendition of Billy Joel’s “Piano Man.”
11. Conan Visits A Sick Writer
Writer Michael Koman felt bad about calling out of work so he sent in some material for the show, not realizing it would apparently read so weakly that Conan would feel the need to pop in at his apartment to make sure he was really sick. The result is an awkward and real exchange between a boss and a writer who told me he didn’t quite know how hard he could push back.
From Michael Koman, writer:
“Our general dynamic was that he would sort of lovingly anatomize me, and I would bumblingly try to do the same thing to him, but I would usually just say something way too blunt and mean. But I think that basic relationship is why it made some kind of sense for him to go to my apartment to see how I could possibly have been sick enough to justify the horrible page of ideas I had sent in that morning.”
Here’s an interesting detail: in the original episode, Koman makes a remark about his doorman letting Conan up which caused consternation with his Super resulting in him editing out the remark for reruns (at the Super’s suggestion).
10. Sattelite TV
https://www.youtube.com/watch?v=n4LoZz-r1pE
If you love Interdimensional Cable on Rick And Morty, allow me to introduce you to Sattelite TV from Late Night, a recurring platform for bite-size bits too weird to live as full sketches. This includes a guy who starts every conversation singing a modified version of Men Without Hats’ “Safety Dance,” a court show where a potato judge presides, a golden retriever doing ventriloquism with a dog puppet, Amy Poehler and Matt Walsh as a dysfunctional married couple trying to deliver the news, and Mike Sweeney as Abraham Lincoln in “The Lincoln Money Shot Channel.” Every one of these could be an Adult Swim show. These are just the scraps, proving how next-level talented the show’s writing staff has been.
9. Jack McBrayer and Triumph Go To Weiner’s Circle In Chicago
https://www.youtube.com/watch?v=33zPlnhymCU
As Mike Ryan alluded to in his talk with Smigel about Let’s Be Real, the velocity of Smigel’s mind is off the charts. That’s why Triumph is as good and as legit iconic as it is. But in this instance, it’s a whole other type of amazing watching Smigel’s mind work while getting back as good as he gives from the crew of the Weiner’s Circle in Chicago, a spot renowned for talking smack to their customers. It’s not people distracted by the puppet and the situation they’re in at a dog show or on line for a movie (each examples that would place high on any top sketch list if that was all this was). Here, sparks fly and the whole time you are physically frightened for gentle Jack McBrayer’s dear sweet disposition.
8. The Masturbating Bear
https://www.youtube.com/watch?v=zf-EPhNRBi8
Of all the show’s brilliant one-note characters, the Masturbating Bear was the onanist. You knew what he was going to do, and yet, you laughed every single time because it’s the wildest god damn thing that it popped up on NBC just a few short hours after an episode of Wings. Here, the setup is everything. The Masturbating Bear’s mom is sick and he needs to enter a Million Dollar Money Box to save her life. You know what happens… magic.
7. The Walker Texas Ranger Lever
https://www.youtube.com/watch?v=K2_SvX4PEbU
A few inside tidbits from longtime Conan writer Mike Sweeney, Koman, his writing partner Andrew Weinberg, and propmaster Bill Tull. First, the Walker Lever exists somewhere in storage. Second, this all started because of the notion that the NBC/Universal merger meant the show had free reign to show clips from Walker Texas Ranger at will. They did not. Which is why they stopped eventually. But in its time, god damn was it magnificent. Such a simple premise: pull a lever, get a prize. And the prize was a seemingly random (though painstakingly discovered by Koman and Weinberg through hours and hours of research) clip of Chuck Norris getting dragged across a field or of a pre-Sixth Sense Haley Joel Osment matter of factly telling a group that he has AIDS. “We waited a year before we showed that clip,” Sweeney told me, reflecting on concerns about the censors. It’s not even technically a “lever” clip in the above video, but still a part of the legend. And while the bit eventually came to a close, they tried to walk away multiple times before it was finally shut down. Including after they had Chuck Norris on the show to add a meta send-off.
From Mike Sweeney, writer:
“We thought that would be the end of it. We’re like, okay, we’ve don’t it. I don’t know, 15 times? Doing something that many times, we felt like, okay, it’s run its course. Let’s end it and bring on Chuck Norris and we’ll never do Walker Texas Ranger Lever again. That’s it. It was a nice ride. […] I think nine months went by and we had two weeks off and Conan came back from break and he said, ‘All anyone’s saying to me everywhere I go is you’ve got to keep doing more. We need more Walker clips.’ I was like, ‘Okay.’ I had to go to Michael and Andrew and I was like, ‘Guys, sorry to tell you, but you’ve got to screen more.’ They’re like, ‘There can’t be any more clips.’
But it was an endless supply. They went down and found more great clips and we ended up doing it again for another two months. Then we stopped again. The same thing happened again nine months later. Fans on the street were like, ‘Come on, show more clips.’ I think there was a third round of it.”
6. Conan Without Borders: Haiti
https://www.youtube.com/watch?v=k-f_wQjRflc
Save for some of the Clutch Cargo stuff from back in the day and monologue jokes across multiple decades, Conan has largely avoided being overtly political on the show. When I spoke with Andy Richter last year, he had a great line about why not: “Conan actually said to me once, ‘There are all kinds of people doing topical stuff and making political points,’ and he said, ‘It’s so much more interesting to me to just be silly and be absurd and explore the absurd, and ultimately I think it’s doing a greater service to humanity.’”
But with reports that President Trump called Haiti a “sh*thole” country, Conan seemingly took it as a challenge, prompting a herculean effort to quickly do a Without Borders from the country. The whole thing is funny, as per usual with the long, long history of Conan visiting other countries, but there’s an empathy that’s so palpable and paired with a want to cut through the mountains of nonsense. Conan isn’t the first person you think of when it comes to getting heavy and making a statement piece, but that doesn’t mean he hasn’t done it or that it isn’t powerful. Reference remarks following school shootings, the aftermath of Robin Williams’ death, and the first episode following 9/11 where he plainly talked about not knowing how to do the job of being an ass and making people laugh in that exact moment. But with Haiti, he made more than a statement, he made an impact, taking a camera right to the spot and countering an idiot’s verbal diarrhea with a window into the vibrancy, resiliency, and nuance of a whole country.
5. Conan Visits Hunter S. Thompson
https://www.youtube.com/watch?v=wKq5wmCz0wM
You can’t be great at interviews if you aren’t open to going where the guest wants to go. Even if that means not so much an interview as a trip into the woods to “shoot guns and drink hard liquor” in the name of creating art with literary literal madman Hunter S. Thompson. What more needs to be said about this moment?
“F*ck you, bear!”
Well, there it is.
4. The Paul Rudd Mac And Me Surprise
https://www.youtube.com/watch?v=9rcqGBrHDtw
Much like the Masturbating Bear (which is an. aces way to start a sentence), we always knew what was going to happen when Paul Rudd popped up on any of the three iterations of Conan’s shows. He’d do the usual talk show stuff, everyone would laugh and then the time would come for a clip and you’d kinda forget. It was like setting a trap. It’s the perfect bit, made richer by the fact that it might be late night’s most enduring tradition.
3. Old Time Baseball
https://www.youtube.com/watch?v=GS39vMhag-A
There are times when Conan approaches a situation as something of a blank canvas to see what can be made. Those fishing expeditions. But then there are other times when it feels like he’s trying to either solve a puzzle or flip over the table that it’s on before laughing and pointing. That’s the takeaway from Old TIme Baseball, which might be universally regarded as among the top things he’s ever done. He walks onto the field like an Alien crash-landed and accumulating data: is there an accomplice? What can he learn about these people from their uniforms and how everyone is speaking and engaging like it’s really the 1860s? And then he tries to infiltrate, taking an at-bat, threatening to throw hands, and being scared of technology. It’s playful enough to be a little pointed and pointed enough to be hilarious. And wow, how many times has the show walked that line successfully?
2. Conan Goes To Houston To Find Viewers
https://www.youtube.com/watch?v=IQs_oRJtcno
Speaking of, Conan is calling upon many of the same superpowers here but he’s also got no clue what he’s going to find of comic value in Houston late in the night. Enter Buffalo, a big dude who seemed like he might be persuaded to chose violence and who didn’t seem like he’d be down to absorb Conan’s brand of playfulness or pointed remarks. It’s great when things work, it can be even better when they don’t workout and Conan wasn’t afraid to show those moments.
Additionally, going someplace in search of people who recognize you is such a great send-up of Hollywood phoneyness, affiliate relations torture, and a manifestation of the self-deprecating nature of the show and its host.
1. Conan Discovers Late Night Is An Undercover Sting Operation
https://www.youtube.com/watch?v=fQEs3Irurgw
There was a distinct vibe that the show was always running from the reaper in its early days. Perhaps that’s why this sketch lands so perfectly. Or perhaps it’s in the commitment level and the performances — particularly Richter, who carries the bulk of the story. I could have picked any number of moments or characters to top this list, but while so many favorites come together while they’re filming, there is something to be said for a truly great produced bit and something that is super well-coordinated and choreographed. Like a ballet, really.
The Conan team has, for the longest time (and I’m refusing to use the past tense here since the HBO Max show is coming and will still be late night to me), shown an ability to create comedy from nothing and to find a way to get laughs out of the most esoteric, 2 AM in the morning on a napkin bits of weirdness. All in their pursuit of a challenge, or expressing a wholly new idea, and in that pursuit of the cross-section of silly and stupid and magical that Conan talked about in the TBS series finale. It’s a huge part of their charm, but they are also master tacticians and craftspeople.
From the costumes to the props to the performances and the material, we’re getting an idea fully realized in moments like the above sketch where they refuse to settle for the passing grade. They want to take it to the end of the line and they do here, with an empty studio, Conan robbed of his life’s work, and being made fun of for still believing in his life.
Whether their commitment is for you or for them isn’t quite clear, maybe both? But it’s definitely for the sake of doing the thing right and making sure it sticks with you. And that thing, as well as all the other things expressed here, make Conan a multi-generational talent and, I feel, late night’s greatest host.