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MISS: Bobby Brown
Mr. “My Prerogative” started in New Edition when he was 9 and then went on to have a successful solo career as a purveyor of the New Jack Swing movement. As his drug use and mental issues ramped up, most notably with ex-wife, the late Whitney Houston, the hits quit coming. Earlier this year, Brown, now 44, briefly went to jail for DUI. (That’s Brown in the red sweatshirt in the video).