Hip-hop is probably one of the last things that comes to mind when you think of the 68-year-old David Letterman, but the genre has a surprisingly great history on The Late Show. Appearances were scarce in the opening and closing years of the show (especially the latter), but for a time Letterman showed love to some of the best MCs in the game—up-and-coming and already established. The 2000s were particularly lush, with multiple performances from the likes of Jay Z, Kanye West, OutKast, and more. As we prepare for Letterman to go off the air after more than 30 years, we're celebrating his storied career the best way us hip-hop heads know how by counting down the best acts he's welcomed on the show.

Ian Servantes is a writer living in Colorado. Follow him @ian_servantes.