The 25 Best Hip-Hop Performances on 'The Late Show With David Letterman'

The genre has a great history on the show despite limited appearances.

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Complex Original

Image via Complex Original

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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.

26. Tyler, the Creator f/ Earl Sweatshirt and Domo Genesis “Rusty”

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25. Ginuwine f/ Missy Elliott “Get Involved”

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24. Busta Rhymes Medley

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23. Black Eyed Peas “Let's Get It Started”

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22. The Black Keys f/ Mos Def and Jim Jones “Ain't Nothing Like You (Hoochie Coo)”

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21. Eminem and Jay Z “Not Afraid” and “Renegade”

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20. J. Cole “Be Free”

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19. Kid Cudi “Pursuit of Happiness”

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18. Kanye West “Love Lockdown”

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17. The Roots f/ Chrisette Michele and Wale “Rising Up”

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16. Lupe Fiasco “Superstar”

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15. Beastie Boys “Sabotage”

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14. The Roots “Here I Come”

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13. Jay Z “Roc Boys”

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12. Nelly “Hot in Herre”

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11. Kanye West f/ Syleena Johnson “All Falls Down”

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10. Lupe Fiasco f/ Jill Scott “Daydreamin'”

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9. Jay Z f/ Mary J Blige “Can't Knock the Hustle”

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8. OutKast “Roses”

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7. Keri Hilson f/ Kanye West “Knock You Down”

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6. Mos Def “Quiet Dog”

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5. Busta Rhymes Medley

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4. Fugees f/ A Tribe Called Quest and Busta Rhymes “Rumble in the Jungle”

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3. OutKast “Hey Ya”

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2. Beastie Boys “Ch-Check It Out”

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