David Letterman reinvented himself with My Next Guest Needs No Introduction, which premiered on Netflix in January 2018. Bushy beard, minimalist set, exclusively high-profile guests, deep conversations — riveting stuff, but a much more mature style than the concoction of absurdity and snark that defined his innovative TV work from the '80s and '90s.

After emerging as a stand-up comedian in '70s (notably debuting on Johnny Carson's Tonight Show in 1978), Letterman first entered the wider cultural mainstream in 1980 with his shortly lived NBC morning talk show. But his reign as late-night's resident wise-guy began on Feb. 1, 1982, with the premiere of Late Night With David Letterman, which ran until June 1993. That show introduced all of his signature comedic traits: that gap-toothed smile, the irreverence of his field segments, an often-deadpan interview style. And his legend grew only deeper after leaving that network for CBS, where he hosted The Late Show from Aug. 30, 1993, until May 20, 2015.

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To mark the anniversary of Letterman's final Late Show episode, we've rounded up 18 of the host's most memorable moments from either show — inevitably focusing on his most famous interviews, which range from illuminating (Warren Zevon) to controversial (Madonna) to almost unclassifiable (Andy Kaufman, Crispin Glover, Harmony Korine, Joaquin Phoenix). We also incorporated some of the best musical performances (Future Islands), stand-up sets (Norm MacDonald) and recurring bits (like, well, throwing stuff off the roof) that have become classics in the host's comic universe.