A Definitive Ranking Of Conan O’Brien’s Funniest Side Characters

12.01.16 1 week ago 28 Comments

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All this week, Uproxx’s Late Night Week will take a look at late-night past, present, and future, from talk shows to late-night comedy, and beyond. Here’s a ranking of longtime talk show host Conan O’Brien’s best side characters over the years.

Conan O’Brien may be among late night’s “old guard” these days, but the host of Conan on TBS (not to mention Late Night and The Tonight Show before it) remains one of the format’s most innovative personalities. Nowhere does this distinction manifest itself more than in the many side characters who’ve frequented, and continue to frequent, O’Brien’s stage. From the maniacal giddiness of co-host Andy Richter’s “little sister” to Triumph the Insult Comic Dog’s roasts of Star Wars fans and Westminster Kennel Club Dog Show, here’s a ranking of Conan’s funniest fictional guests.

15. Little Jay Leno

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Employing a little person to play Tonight Show host Jay Leno during his time on Late Night made sense for O’Brien in the ’90s. They were still colleagues at the time, and as Austin Powers: The Spy Who Shagged Me proved later that same decade, smaller actors playing miniature versions of famous people practically guaranteed laughs. Little Jay Leno wouldn’t translate well for today’s late night audiences, but considering what would transpire between the real Leno and O’Brien during the renewed “late night wars,” this character’s profile moved up a few notches.

Best character trait: His proportionally massive chin.

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