92. RICK ROSS
The boss of the South likes to slang rhymes about slinging rock, but according to the Smoking Gun, the only hard time he did in Dade County was on the other side of the law: although he refuses to admit to it, he reportedly served 18 months as a corrections officer. For a rapper, that’s about as sexy as blowing your hype man on stage. As it is, Ross is so ugly he keeps his sunglasses on at all hours — even when traumatizing a Fader TV interviewer by whipping off his shirt to reveal his numerous tattoos . . . and his (bigger-than-Trina’s) man-tits.