There's probably not a rapper in the world that would want to trade careers with JoJo Simmons, but the same can't be said about his bank account. The son of hip-hop great Rev. Run has his advantages --  living in a mansion, avoiding jail time and lots of money -- but it doesn't necessarily guarantee you a successful rap career. JoJo's attempts at dropping bars has sparked more feuds than fame, and while he's no doubt proud of little brother Diggy, on some level it has got to hurt.