Freekey Zekey

It's easy to see that Dipset rapper Freekey Zekey has bad luck. Not only was he shot and robbed in April 2003, but when he came to, he found that he'd been arrested on a slew of pre-existing drug warrants. Instead of spending the next three years popping bubbly (and other things) as his Dipset comrades Juelz Santana and Cam'ron were experiencing their biggest successes to date, Freekey was looking over his shoulders at Durham Correctional Center in Durham, North Carolina. Zekey was finally released from prison in 2006 and resumed his position as president of Diplomat Records. His solo debut, The Book of Ezekiel, dropped in the summer of 2007.