Lupe vs. Obama (June 7, 2011)

Since he first stepped on the scene Lupe Fiasco has been considered an intelligent, politically astute rapper. Which is why so many of his fans were bewildered when Fiasco called President Barack Obama 'the biggest terrorist” during an interview on the CBS-affiliated internet video show “What's Trending.”

Fiasco's statement became, well, a fiasco—drawing criticism from all corners, including Fox News talk-show host Bill O'Reilly, who called Fiasco a "pinhead" on his show The O'Reilly Factor. Smelling a ratings bonanza, O'Reilly also extended an invitation to Lupe Fiasco to come on the show and defend his stance. When Fiasco accepted the invitation and appeared on the show, he stood behind his criticism of President Obama and has yet to back down.