Wilson's solo career begin with 1956's "Reet Petite", written by Berry Gordy Jr, then an unknown who would later go on to write many of Wilson's other hits, such as "Lonely Teardrops" and "I'll Be Satisfied". Wilson's brand of pop-soul and R&B helped him cross over to the mainstream, having several pop hits. In the 1960s, Wilson continued to record singles, many of them operatic and overblow, such as "Danny Boy" or "Night", others were uptempo and exciting, such as "Baby Workout" in 1963. Wilson was shot and wounded by a female fan in 1961.
His career began to suffer in the mid-60s, though he managed a brief revival by collaborating with Carl Davis, a legendary Chicago producer. This resulted in two hits, "Whispers" and "Higher and Higher". The revival was short-lived, though, and Wilson rarely charted in the 1970s. Wilson suffered a heart attack while playing a Dick Clark show at the Latin Casino in New Jersey in 1975; he was singing "Lonely Teardrops". A comatose Wilson lived in a hospital until dying in 1984.