Conan O’Brien has no interest in being limited to the confines of a studio or even a continent. Out in the world, there are interesting sights and people to meet, and real human comedic moments that can’t be equaled by bit players in a comedy sketch.
It’s worth it to take a camera crew to a place that is far away or at least under-explored. Late night comedy can’t just be about topical monologue jokes. You’re trying to fill an hour of television on most nights of the year and the guests only get you half way.
It’s what a host does between those two pillars (the monologue and the guest interviews) that often defines their legacy. For Conan, that legacy is rich thanks not only to old timey baseball, The American Girl Doll Store, and his trips to far off places like Ireland and Cuba, but also this collection of somewhat obscure remotes from Conan’s somewhat wilder Late Night days.
A Random Hotel That Conan Stayed At Once
I moved around a lot as a kid — all over the east coast — and as a result, I get caught up in nostalgia whenever I’m near a place that I used to live. It’s an entirely silly thing that feels hollow immediately after the euphoria of a found memory fizzles away, but in this early clip from Late Night, Conan seizes on that wistful need in us all to see the past again. And he does it in a random hotel room that he stayed at once. It’s a brilliant takedown of our inherent nostalgic tendencies that is even more relevant when you think of how much of our culture is now wrapped up in reflection. Now please continue to read this list about late night comedy sketches that I loved when I was a teenager.
There is a winning formula for Conan O’Brien’s remote segments and it’s pretty basic: put Conan in a typical situation and let him walk around until he finds something mundane that inspires him to go to a weird and wonderful place. At the flagship F.A.O. Schwarz store in midtown Manhattan, those mundane objects were a lightsaber that he used to lightly threaten a child, a hybrid skateboard, and a big-breasted stuffed orangutan that Conan used for his depraved gropey pleasure.
Conan Helps One Of His Writers Find An Apartment
Before there was Jordan Schlansky, there was this Andy Blitz co-starring video where Conan tried to help him find an apartment on a Late Night writer’s salary. The results are hilarious largely because Blitz is, unlike Schlansky, an active participant in the comedy and not just someone for Conan to react to. But you can’t discount the real estate agent’s contribution, either.
I don’t know if Conan has mellowed or if people are more accepting and aware of his shtick, but it just seems like the comedy in Conan’s more recent remote segments doesn’t come from awkwardness and the art of making people just uncomfortable enough so that they don’t punch you. This remote and the real estate agent’s palpable annoyance are a great example of when that wasn’t the case.
The Blizzard of 2003
Conan is unleashed upon the city during a blizzard that, if I remember correctly, dropped like two feet of snow on New York. The main reason this is on here is for Conan’s repeated attempts to knock a stranger off of a tall snow bank. It’s probably scripted, but it doesn’t look like it and things get uncomfortably physical in a delightful way. It’s also fun to just watch Conan people watch and react to what he’s seeing — like the cross country skier in spandex that slid past him during the segment.
Conan Goes To Houston
A personal favorite that has stuck with me like swallowed gum; this remote takes Conan O’Brien to the un-glamorous dreamscape that is Houston after midnight in search of viewers who will watch his show and ignore the fact that he was, inexplicably, on at 2:40 in the morning in that market. Visits to a local strip club, the Astrodome, and an emergency room follow, but the shining moment comes at a bus depot near 3 a.m. when Conan meets a man named Buffalo that will change his life.
Buffalo was and probably still is (you can’t keep a Buffalo down) a man of stout body and mind with a powerful face bush and a muscle shirt who knows all about Conan’s “crappy” TV show and is disappointed by Andy Richter’s absence on the trip. “It’s not a show without the little fat dude,” he says, and he is so right.
Shootin Guns And Drinkin Hard Liquor With Hunter S. Thompson
This isn’t obscure, but it’s unhinged and something I love more than adhering to the arbitrary guidelines that I set for myself when I started this.
Hunter S. Thompson was a mad man and a fire-breathing dragon who was on our side. When he made occasional appearances on Letterman’s version of Late Night, it was bizarre but he was still on someone else’s turf (wherever that happened to be) and he had to (mostly) play by their rules.
In this visit to Thompson’s homestead, the iconic writer makes all the rules and it feels like a field trip into his amazing and tripped out mind. A place where you pick-up your weapon and your whiskey at the bar and then shoot up cardboard cutouts and your books in the name of creating “art.” Add to that the assassination of a different large stuffed monkey and a cry of “F*ck you, bear!” and it becomes a three minute testimonial for the kind of weird stuff that lived on television in a less polished age when things were less staged and hosts like Conan were willing to buy the ticket and take the ride.