Year: 1998
Ride:
Bentley Azure

It's a simple image, and yet an instantly classic one. The New York throne was for the taking in '98, and after two great yet then underrated albums, Jay-Z was ready to make his presence loud and clear and the album cover had to make a statement along with the music. Enter go-to album photographer Jonathan Mannion and that now iconic Bentley Azure. With that casual stance, Jay-Z had finally arrived, and so began the never-ending onslaught of next-level flossing.