28. Method Man & Redman "Da Rockwilder" (1999)

Director: Dave Meyers

Sure, this video had a lot going for it: Some cool special effects, explosions, and the always animated Red and Meth doing, well, rambunctious rapper things, in an post-apocolypic sewer-factor-empty-strip-club type-joint. But the video also featured a memorable "WHUH?" moment as it broke between Meth and Red's verses, to cut into a parody of those '90s Gap ads, one of the most successful marketing campaigns ever. We can totally see a movie executive hesitating at the idea of casting Red & Meth in How High only to see this video and the phrase, "Everybody In Stank Butt Jeans," laughing out loud, and saying, "Greenlight it." The video then cuts back in, and Red and Meth are now strolling through the factor-strip-club-nuclear-warhead-storage-facility, except they're tethered together, doing a proto-Jerome Robbins dance routine together unlike anything two straight male rappers have done quite since. It's weird as shit, and fun, and brilliant.