30. LL Cool J "Mama Said Knock You Out" (1990)
Director: Paris Barclay
LL is known for having a crazy physique, but compared to his later days, LL doesn't look like a bodybuilder in this video. None of that matters, though, since his bars are in top shape and this clip-one of the most crucial links in establishing the cultural bridge between boxing and rap-is more about his presence and confidence than anything else. Rappers have done the "rapping into the mic" things in plenty videos, but here, with LL's rugged rhymes placed in the context of a boxing ring, at the time of its release, it meant so much more.