Year: 2010

No one wants to be that guy who makes a few hit records, blows all his money, and then become a hip-hop punchline. But that's basically what happened to MC Hammer. So when Jay-Z rapped "I lost 30 mil, so I spent another 30/Cause unlike Hammer, 30 million can't hurt me," on Kanye West's "So Appalled," Hammer got pissed. So pissed, in fact, that he decided to release the hilariously awful diss track, "Better Run Run" in November 2010. Soon after, the Oakland hitmaker claimed he deaded the beef because he believed he'd made his point—whatever that may have been. Jay-Z, on the other hand, thought he took it the wrong way. The funny part about all this? Neither of these guys is that young—Jay-Z is now 42 and Hammer is 50. But pathetic stunts like these make Hammer look closer to 86.