Shirley's first album as a leader was "Tonal Expressions", for Cadence Records. It reached No. 14 on "Billboard"'s Best-Selling Pop Albums chart in 1955. During the 1950s and 1960s, he recorded many albums for Cadence, experimenting with jazz with a classical influence. In 1961, his single "Water Boy" reached No. 40 on the "Billboard" Hot 100 and stayed on the chart for 14 weeks. He performed in New York City at Basin Street East, where Duke Ellington heard him and they started a friendship.