Dated: 2010

Though Chelsea Handler's love of all things rapper is well-documented on her talk show, most assumed it was all part of her routine. That is, until 2010, when Handler started dating 50 cent. The match seemed unlikely: she was raised in an upper middle class neighborhood in Jersey; he grew up across the river in South Jamaica. She loves vodka; he doesn't drink. She helped shoot a TV show; he has been shot nine times. Unsurprisingly, the two opposites didn't stay attracted to each other for long.