5. The Notorious B.I.G f/ Puff Daddy & Ma$e "Mo Money, Mo Problems" (1997)
Director: Hype Williams
Puff Daddy and Mase are in this video wearing matching yellow shiny suits and FLOATING in a nondescript silver space tube while Kelly Price wails a Diana Ross interpolation on a flat screen television behind them. Is there anything else to discuss? Actually, yes, there is: The duo parody Tiger Woods and Bryant Gumble, casually coast in front of cash explosions, and wave their Rolex watches side-to-side better than anyone in history. "Mo Money Mo Problems" is actually Biggie's record, and his verse is still the best thing about the song, but the video is when Puffy officially took on the burden of being an artist, in a massive way, and it worked.