Legendary as the first gangster rapper ("P.S.K. What Does It Mean?"), the "50ish" native Philadelphian has a cult following and describes himself as "an artist who sometimes raps, musician, deejay, actor and film composer." A/k/a Jesse Bonds Weaver Jr., he says his dream date is "waaaay too dirty to print. It involves cake, Tina Fey, sushi and leather."

Swim trunks: 2(X)IST

Twitter: @SchoollyD