He worked as a copy boy and runner for the Associated Press in Manhattan, but wanted to become a professional singer. He performed as a singing waiter in several Italian restaurants around the borough of Queens.
Bennett fought in the final stages of World War II as an infantryman with the U.S. Army in the European Theatre. He later described his experience as a "front-row seat in hell."
Upon his discharge from the Army and return to the U.S. in 1946, Benedetto studied at the American Theatre Wing on the GI Bill. He learned the "bel canto" singing discipline, which would keep his voice in good shape for his entire career.
Based upon a suggestion from a teacher at American Theatre Wing, he developed an unusual approach that involved imitating, as he sang, the style and phrasing of other musicians—such as that of Stan Getz's saxophone and Art Tatum's piano—helping him to improvise as he interpreted a song. He made a few recordings as Bari in 1949 for small Leslie Records, but the songs did not sell.
In 1949, Pearl Bailey recognized Benedetto's talent and asked him to open for her in Greenwich Village. She had invited Bob Hope to the show. Hope decided to take Benedetto on the road with him, but suggested he change his name to Tony Bennett. In 1950, Bennett cut a demo of "Boulevard of Broken Dreams" and was signed to the major Columbia Records label by Mitch Miller.
In 1951 had his first number one popular song with "Because of You," a ballad produced by Miller with a lush orchestral arrangement from Percy Faith. It started out gaining popularity on jukeboxes, then reached #1 on the pop charts in 1951 and stayed there for 10 weeks, selling over a million copies.
This was followed to the top of the charts later that year by a similarly-styled rendition of Hank Williams's "Cold, Cold Heart," which helped introduce Williams and country music in general to a wider, more national audience. Miller and Faith continued to work on all of Bennett's early hits.
Bennett's recording of "Blue Velvet" was also very popular, and, several top hits such as "Rags to Riches" followed in the early 1950s.
in 1962, Bennett released what was to become his signature song, "I Left My Heart in San Francisco." Although the song only reached #19 on the Billboard Hot 100, it spent close to a year on various other charts and increased Bennett's exposure.
The album of the same title was a top 5 hit and both the single and album achieved gold record status. The song won Grammy Awards for Record of the Year and Best Male Solo Vocal Performance. In 2001, it was ranked 23rd on an RIAA/NEA list of the most historically significant Songs of the 20th Century.
Bennett's next album, I Wanna Be Around also made the top 5, with the title track and "The Good Life" each reaching the top 20 of the pop singles chart along with the top 10 of the Adult Contemporary chart. His career and his personal life then suffered an extended downturn during the height of the rock music era.
Bennett staged a remarkable comeback in the late 1980s and 1990s, putting out gold record albums again and expanding his audience to a younger audience while keeping his musical style intact. He remains a popular and critically praised recording artist and concert performer in the 2000s.
Among his other honors, Bennett was inducted into the Big Band and Jazz Hall of Fame, 1997 and received a lifetime achievement award from the American Society of Composers, Authors, and Publishers in 2002.