“In 1993 Johnny Carson gave me the best advice of my career: ‘As soon as possible, get to a streaming platform,’” O’Brien said in a statement. “I’m thrilled that I get to continue doing whatever the hell it is I do on HBO Max, and I look forward to a free subscription.” At first glance, this appears to be bittersweet news. O’Brien has been a late night talk show staple for decades. Following an excellent writing career for The Simpsons and Saturday Night Live, O’Brien took over for his hero David Letterman on NBC’s Late Night in 1993 and stewarded it through 2009. That was followed by a measly half-year as host of the venerable Tonight Show before NBC got spooked about not having Jay Leno on TV anymore. For the past 10 years, O’Brien has continued his late night talk show format for TBS’s Conan. Though it’s sad to lose O’Brien as a late night talk show titan, the reality is that the comedian was never much of a talk show host to begin with. That’s not to say that he wasn’t good at the job, because he was. But it’s always been evidently clear that O’Brien succeeds the most when not tied to the restrictive talk show format. This is something that the host himself has increasingly realized over the years, cutting out an interview segment slot from Conan to bring the running time down to a breezy 30 minutes, and producing the acclaimed Conan Without Borders series to capitalize on his already popular remote travel segments In honor of O’Brien finally making the long-awaited jump back to variety comedy, we’ve gathered together our 10 favorite remote segments the comedian has ever done. The only qualifications here are that the bits have to have occurred on one of his three major shows and they have to feature him away from his studio. Also, we won’t be counting any official Conan Without Borders entries as that is a distinct entity and would muddy the waters too much. Without further ado…
Honorable Mention – Triumph the Insult Comic Dog Attends the Premiere of “Star Wars: Attack Of The Clones”
(Original airdate: 5/17/2002) Sadly, Triumph the Insult Comic Dog is not Conan O’Brien and therefore cannot appear on this list of Conan’s best remote segments. But it would feel unfair not to take time to highlight Late Night with Conan O’Brien’s other remote segment superstar. As created by SNL’s Robert Smigel, Triumph is a Eastern European-accented, cigar-chomping insult comic…who also just happens to be a dog puppet. Triumph’s trips outside the studio are almost always hilarious, but the rude canine hits an absolute comedic high with his trip to the Attack of the Clones premiere. Perhaps the most amazing thing in that clip isn’t the numerous cutting, hilarious, and utterly cruel nerd jokes, but how rapturously the audience responds at the beginning upon learning that Triumph is the correspondent Conan sent to the premiere.
10. Conan’s Trip to Ireland
(Original airdate: 3/17/1999)
9. Conan Delivers Chinese Food in NYC
(Original airdate: 11/1/2011) Late in 2011, just under a year after Conan premiered, Conan returned to New York City where he had spent his Late Night tenure to film a week’s worth of shows. And what better way to ring in the return than with a stellar remote segment? In this bit, Conan serves as an inept delivery boy for Manhattan Chinese restaurant King Wok. It’s apparent early on just how excited he is to be back in New York when he’s already purring at one of the employees 10 seconds in. Conan gets the full New York experience in this, from one standoffish deliveree angrily denying that he’s her delivery guy to him being served Argentinian tea from a beautiful woman leaning out her window. The citizens of New York City are often Conan’s best comedic collaborators and they show why once again here.
8. Conan Goes to Trucking School
(Original airdate: 7/18/1997) “Conan Goes to Trucking School” benefits from having the thinnest of setups. Conan wants to be a truck driver. Why? Well, who cares, the Jersey Truck Driving School is up for it and we’ve got some time to kill. Into that conceptual vacuum steps Conan just having the time of his life. You know you’re in for a good remote segment when Conan and a trucker he just met are singing a country song less than two minutes in.
7. Conan Tries to Sell His Ford Taurus
(Original airdate: 5/6/2004)
6. Conan Visits The American Girl Store
(Original airdate: 12/18/2013) “Conan Visits The American Girl Store” is perhaps the best argument you can find for giving Conan O’Brien alcohol and putting him on television. The first half of this bit is undoubtedly solid as Conan plays up the creepiness of him visiting a store designed for young girls. But things really take off when he finally chooses his doll (Potential Nazi war criminal Agnes Schweitzhoffer) and settles in for dinner in the American Girl Store’s shockingly lush dining room. As the chardonnay goes down, Conan (and Agnes by extension) are increasingly unable to hide their annoyance at the garçon and all his stupid riddles.
5. Conan Goes to Houston to Find Viewers
(Original air date: 5/1/1997) In the first few years of Late Night with Conan O’Brien’s run, Conan and his team of writers had plenty of fun with how little people seemed to enjoy their dumb show. This segment takes that concept to its extreme. When Conan discovers that the Houston television market doesn’t air Late Night until 2:40 a.m. local time, he takes a camera team to Texas to find some fans after hours. The journey takes him from a bail bonds office, to a hotel basement, to an emergency room, and all the way to a bus terminal at 3:21 a.m. where he meets a man who is decidedly not a fan. “I was just almost murdered,” Conan says as he sits down for comedic effect…but also probably to catch his breath.
4. Ice Cube, Kevin Hart, and Conan Share a Lyft Car
(Original airdate: 12/10/2013)
3. Conan Plays Old-Timey Baseball
(Original airdate: 6/25/2004) When Conan signed off of Late Night for what would be an unexpectedly brief Tonight Show tenure, he brought back this 2004 skit as an example of the kind of absurdist humor he felt the show did best. And it’s clear to see why. Conan’s trip to Old Bethpage Village Restoration where reenactors play old-timey baseball is in many ways the goofy platonic ideal of a Conan segment. The absurdity of the premise is funny enough as is, and then Conan’s buy-in only enhances the proceedings. “What is that demonry???” a 19th century Conan cries as a plane passes overhead. But the not-so-stealthy MVP here is the reenactor who is truly committed to her role as the dour village woman with a dead father and a soon-to-be-dead husband in the Civil War. “You know that guy ain’t coming back. I was down in the Civil War. I saw him and he was acting very cowardly I have to say,” Conan says in an attempt to woo her.
2. Dave Franco and Conan Join Tinder
(Original airdate: 7/17/2014) Just about every moment of “Dave Franco and Conan Join Tinder” is joyously, ludicrously hilarious. Conan gives viewers all the set up they need for why he’d want to browse Tinder with Dave Franco, saying “Naturally, because I’m a creep, I’m intrigued.” Conan and Dave adopting their Chip Whitley and Dgenghis Roundstone (the “D” is silent) personas is wonderful. As is an unexpected cameo from Conan’s assistant Sona and Conan and Dave’s competition over the 74-year-old Gloria. But per usual, this thing really gets moving when Conan and Dave hit the road in their creepy panel van. Conan assures Dave that the van is filled with duct tape solely to hold the cameras up. “I wish I could say I saw duct tape on any of these cameras,” Dave responds. Once Chip and Dgenghis finally meet their Tinder date, this segment evolves into its glorious final form where Dave and the citizens of L.A. bond over what a weirdo Conan is.
1. The Jordan Schlansky Saga
(Original airdate: 9/1/2008) Schlansky is just an aggressively strange person. Always dispassionate and rarely smiling, Schlansky fancies himself a Bohemian renaissance man with his breakfast shakes, mastery of the bullwhip, and vespa. The best part of their original meeting is when Conan realizes just how hilariously bizarre the gestalt of Jordan and can’t help but collapse into laughter as he chokes out “You’re just not like other people.” Later Jordan would join Conan and many remote segments to aggressively annoy and vex him, including one dinner that is among the best things the show has ever done. That lead to Conan’s truly chilling villain monologue: Conan: I promise you this, I will not kill you myself. But I will have you killed. I will have you wiped out. Jordan: I am subject to the same winds, the sun, the air that created the wine that I am drinking. Conan: There will be nothing that links me to your murder. There will be no physical link between your dead body and myself. But you will be murdered. I will order it. I will pay for it. But I’ll have no- I am blameless in the eyes of the international court, that I promise you. (laughs) I’m gonna kill you. (laughs) You have to go.
BONUS – Conan Checks Out the Christmas Lights in Dyker Heights
(Original airdate: 12/22/2000) Here’s a bonus entry for purely sentimental reasons. This is nowhere near the best of Conan’s hundreds of remote segments, but it holds some personal value to your dear author. Once upon a time I was a child celebrating the Christmas season a month after my family’s 400-mile move to a new home. My parents had a Christmas party that day and I severely overindulged on chocolates, finishing them off with several clementines before bed for some reason. Suffice it to say, sometime around midnight, I puked all over a brand new sleeping bag I received as a gift and ended up on the couch, full of chocolate, clementines, and regret. My mom flipped on the TV to distract me while she hauled off the sleeping bag to be cleaned…or burned. On TV was this very segment “Conan Checks Out the Christmas Lights in Dyker Heights.” I was enraptured by this strange orange-haired man making fun of people’s garish Christmas decorations…even as I tasted the foul acidy sting of rancid citrus in my throat. And thus is the perfect Conan O’Brien watching experience. Best of luck at HBO Max, Conesy!
