From 1993 to 2021, Conan O'Brien was one of the biggest names in late-night with his three talk shows between NBC and TBS. But since wrapping up his titular series, Conan four years ago, O'Brien has been keeping himself busy, be it with his radio show Conan O'Brien Radio on SiriusXM or his podcast, Conan Needs a Friend .

Most recently, he's started a whole new chapter and is about to star in his first dramatic role in the upcoming movie If I Had Legs I'd Kick You . But before the movie releases next month on October 10, the role has already given him a career first. It was also the perfect opportunity for O'Brien to do something he had never done on late-night television.

Conan O'Brien Lived Out a Career Dream on 'The Late Show With Stephen Colbert'

During his ap

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