As a member of New Edition, the Boston-raised Bobby Brown honed his image in the ‘80s as the “bad boy of R&B,” grandstanding and showboating to make himself stand out. After going solo, Brown would emerge as the biggest-selling R&B artist of the later part of the decade, releasing the 7X platinum LP Don’t Be Cruel in 1988. (The album continued to chart for the next eight years). The Grammy-winning singer topped off his R&B kingship by marrying the queen of pop, Whitney Houston, in 1992. Unfortunately, in the waning days of his career, Brown became more famous for his run-ins with the law than for his music. But he re-emerged in the pop spotlight in 2005 via his hit reality TV show Being Bobby Brown. A couple of years after the show, Brown and Houston divorced.