Before your favorite rappers were praising Maybachs and Phantoms, they turned to this British line when they wanted performance and ultra-luxury. Everyone from Oprah to Puffy—who in '98 copped the first Azure to touch down on American ground—was seen in the $375,000 four-seat convertible based on Bentley's already beloved Continental models. It wasn't until later that year that a cover appearance on Jay Z's most commercially successful album launched the careers of both the artist and the Azure.

Lyrical Mention: Still got the sky-blue drop-top Azure/Still eat at Justin's in Sean John velour -Diddy, "On Top"

The only thing harder than Jay Z’s one-pant-leg up in his "Hard Knock Life" video was his blue drop top Bentley Azure. So fresh, so clean.