6. T-Pain Apologizes To Jay-Z

Date: September 2009
What Happened: In June 2009, T-Pain embraced Jay-Z’s controversial single “D.O.A. (Death Of Auto-tune)” by joining him on stage during the rapper’s Hot 97’s Summer Jam performance. When Jay-Z was asked about the gesture afterwards, he said, “It was awkward, but it was cool...He didn’t mean any harm.”

But a few months later in Las Vegas, T-Pain lashed out at Jay-Z saying, “Jay-Z is 59 years old. I don't think he has the right to say what's good and what's not. I think if anything is dead, it should be him.” Later that month Pain released a song called “More Careful,” in which he raps, “Some days I wish that I ain't never say shit/ And Diddy said ain't no excuse for what I did/ But I felt like he was knocking the same shit that feeds my kids.” The third verse ends with him saying, “My bad.”

Complex Says: Saying Jay-Z's 59 years old wasn't exactly clever, but it was kinda funny in a "You 36 in a karate class?" type of way.