3. The Notorious B.I.G. "Hypnotize" (1997)
Director: Paul Hunter, Puff Daddy
There were ostentatious videos before, and there certainly were ones after, but Biggie's "Hypnotize" is the prototypical Jiggy Era music video. The shit legitimately looks like a Michael Bay film, and by the 30-second mark, you've already seen helicopters, a speedboat yacht, beautiful women, Cristal, Versace, and piles of cash. The narrative is decidedly ambiguous--we don't know where the hell Big and Puff are going or what they're doing--but (like a Michael Bay movie), who gives a shit? It looks incredible. Like, is it even possible for a 24-year-old rap legend being driven in a Mercedes, backwards, while being chased by motorcycles and a Hummer to not look cool? Then they threw mermaids in there just to fuck with you. Looking back, it doesn't even seem real, but there it is: The most umimpeachably perfect use of an absurd amoung of stunning resources to make a music video.