To urban contemporary listeners, Freddie Jackson is one of the biggest stars of the latter half of the ’80s, dominating the R&B charts seemingly at will. Jackson’s forte was sophisticated, romantic soul ballads aimed at adult audiences, but he was also capable of tackling urban contemporary dance fare and even the occasional jazz tune. Yet unlike many of his peers — Luther Vandross, Anita Baker, Peabo Bryson, etc. — Jackson never managed to cross over to the pop charts, where none of his R&B smashes even breached the Top Ten. As new trends like hip-hop altered the urban contemporary landscape, Jackson gradually faded from view during the ’90s.