When: 1999
Ever since these two dropped the classic battle of the sexes single "Nann Nigga" in '99, there have been rumors. But what do you expect when they were rapping about sex and taking photos like the one above? Truth is, Trina was in love...with Trick's half-brother Derek "Hollywood" Harris, dating for two years until he was shot to death in '94. It's still possible that Trick and Trina hooked up, but we doubt Trick would violate his brother's memory like that. Then again, Trina did say she would "fuck 'bout five or six best friends."
Smash Probability: