When you closes your eyes and thinks about hip-hop, it’s safe to assume you are not envisioning David Letterman.  

While the man himself may not embody our favorite genre, Letterman’s staple "Late Show" on CBS, which airs its final broadcast Wednesday night, has served as a platform for creating career-defining moments for rappers spanning generations. Since its inception in 1993, the "Late Show" has kept the doors of the famed Ed Sullivan Theater open for young stars to establish themselves and establish stars to sustain their light or reinvigorate themselves.

So, without further ado: join us as we take a look at the best hip-hop performances the "Late Show" has ever seen in the only way that our beloved gap-toothed late night talk show host would have it: a Top 10 list.