Diddy

Where: Rolling Stone Magazine cover

When: August 1997

Complex says: A lot was happening for Bad Boy Records that year. Biggie had just passed away; posthumously, his album Life After Death, reached number one on the Billboard Top 200. Diddy was getting ready to drop his first solo debut album, No Way Out. Later that year, Mase released his multi-platinum debut album, Harlem's World.

Diddy was arguably the king of Hip-Hop. Since Versace was still one of the hottest brands in the game, it was only right that Diddy stayed laced in Versace, down to his boxers.