Band Or Solo Artist?: Solo
Genre: R&B, Soul, Pop
Greatest Hit: "Un-Break My Heart" (1996)

Known for many hit singles, as well as an infamous lawsuit with L.A. Reid (which resulted in Braxton filing for bankruptcy), Toni Braxton's undoubtedly had a rollercoaster ride of a career. Fortunately, she got her finances in order and is now the star of her own reality show, Braxton Family.

Though the singer modeled her singing voice after male artists like Luther Vandross and Michael McDonald, she is all woman. Two decades after the release of her self-titled debut album, we can't decide if Toni was hotter at 25 or as the sexy MILF she is today.