Boy George
Boy George was sentenced to 15 months in prison for handcuffing and assaulting a male escort in his hotel room. I couldn’t care less about how good “Karma Chameleon” was. He chained this guy and accused him of stealing his belongings. Bad move all around, George.
Ashlee Simpson
Ashlee Simpson’s demise can be attributed to a tragic Saturday Night Live performance in 2004. The backing track from her first song, “Pieces of Me,” began to play instead of “Autobiography,” and a flustered Simpson attempted to distract fans from the revelation that she’d completely lip-synced by dancing. SNL immediately cut to commercial, and Simpson attempted to blame the band for the mishap.