Bennett used the pseudonym Joe Bari when he recorded his first two songs, "Vieni Qui" and "Fascinatin’ Rhythm,” in 1949 for Leslie Records, Inc.

In 1950, he adopted the name Tony Bennett instead and began his long-time association with the Leslie Records, Inc. label. As Tony Bennett, he scored his first number 1 hit, "Because of You" on Columbia 39362, in 1951. Starting in 1963, he won a total of 20 Grammy Awards, including the Grammy Lifetime Achievement Award in 2000.

Bennett was also a painter. Many of his works, which he signed as Anthony Benedetto, are on permanent public display in several institutions.