14. "Mo Money Mo Problems"
Ostentatious rap videos are still common today, but has there ever been one as fun as "Mo Money Mo Problems?" Probably not. Biggie, Ma$e, and of course Diddy, ball out in wild outfits, float around without gravity, and dance among pyrotechnics. It may not be the most creative video of all time, but Hype Williams captured a moment for rap music, and he made it look so damn entertaining.