Conan O’Brien vs. David Letterman: Who Ya Got?

O’Brien announced he’s leaving late night TV after 28 years. Which iconic TV host reigned supreme? Vote now!

Conan O'Brien David Letterman Split Promo
Left: Getty Images

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Conan O’Brien was an unknown comedy writer when he was plucked from obscurity to replace David Letterman’s Late Night NBC show back in 1993. His razor-sharp wit, self-deprecating sensibility and oddball humor went on to make him a television legend. So when it was announced this week that O’Brien was stepping back from late night TV after 28 years–he’ll leave his Conan TBS show in June 2021–it made headlines around the world. 

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But the carrot-topped comic will still be on a screen near you. His Conan Without Borders travel specials continue to air on TBS, and O’Brien just signed a deal with HBO Max for a new weekly variety series, though no premiere date has been set. He also still hosts his Conan O’Brien Needs a Friend podcast. 

To mark O’Brien leaving late night TV, it makes sense to compare him to his even more iconic predecessor, David Letterman, whose edgy interviews and absurdist skits paved the way for O’Brien and many other comics. For every recurring Conan bit or memorable moment, there’s a Letterman counterpart in a parallel comedy universe. 

While Conan introduced the world to such memorable characters as Triumph the Insult Comic Dog, The Masturbating Bear and Pimpbot 5000, Letterman was spotlighting Larry “Bud” Melman, cracking us up with Top 10 lists and dropping watermelons off the CBS roof. 

Both O’Brien and Letterman are straight-up late night legends, but which TV host reigns supreme? Go to on your phone to predict the winner of this challenge and other fun face-offs!

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