16. 112 f/ The Notorious B.I.G. and Ma$e "Only You (Remix)" (1996)

Album: 112

For starters, you have 112 cruising through New York City, standing in a Hummer with the massive sunroof open. Then there's Biggie rapping in front of a crowd in Times Square, and Ma$e doing the samein a racing jacket. His is red, Puffy's is blue, and 112 looks like a motocross team with their matching gear. These are the type of details you notice anytime you watch this video, and the visuals that remain burned in your brain anytime you hear the song. It all feels very legendary. Like, when else can you recall seeing Biggie out in Times Square rocking a blue polo? That's all it really took to make this video an instant classic. And the requisite Diddy bopping isn't bad, either. Ernest Baker