The original R&B bad boy, Bobby Brown started out as part of boy band New Edition. Though he wasn't the star of the group, he made a point of upstaging frontman Ralph Tresvant, then left in 1986 over a financial dispute. His sophomore solo album Don't Be Cruel was one of new jack swing's banner albums, selling seven million copies and hitting with the title track, “Roni” and “My Prerogative.” Brown's music career since has been plagued with legal issues ranging from drugs to a DUI and several prison stints plus a famously troubled relationship with Whitney Houston. During 2014 he quit and then rejoined a New Edition reunion tour.