In 2016, elegant pop balladeer Johnny Mathis celebrated the sixtieth anniversary of his Columbia Records debut. The golden-toned singer of “Chances Are,” “It’s Not for Me to Say” and “Wonderful! Wonderful!” signed with the label in 1955, a few weeks before his twentieth birthday. With the exception of three years at Mercury Records, he’s been with Columbia ever since, longer than any other artist.

43 Mathis recordings have entered Billboard’s pop singles chart. He’s released 85 albums, exc...