Obscure But Vital ‘Late Night With Conan O’Brien’ Remote Segments Every Comedy Fan Should Know

Features Editor
04.18.15 15 Comments
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.

 F.A.O. Schwarz 

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.

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