Tony Bennett’s 15 Biggest Songs on the Billboard Charts

When Tony Bennett died at age 96 on the morning of July 21, 2023, the world lost one of the last vocal titans of the Great American Songbook.

Bennett – who was born Antonio Dominick Benedetto in Long Island, NY back when Calvin Coolidge was president – enjoyed an illustrious career that spanned nine decades. Post World War II, he began singing in nightclubs using the name Joe Bari, eventually changing his name to Tony Bennett after a suggestion from Bob Hope; Bennett’s final performances were with Lady Gaga – with whom he recorded two top 10 albums on the Billboard 200 — in August 2021 at Radio City Music Hall for the One Last Time concerts.

“I just love the fact that in an era where everything’s based on youth, I can communicate with everybody — the young, the middle-aged and the old like me. I’m very content,” Bennett told Billboard in 2016 of his cross-generational appeal. Bennett’s musical career stood out in two important ways – instead of imitating other vocalists, his vocal stylings were influenced rather by jazz instrumentalists; additionally, the man never chased trends, resisting industry efforts to make him update his sound and style with each passing era. That commitment to his art may have caused him to experience a fallow period in the ‘80s, but by the ‘90s, his fealty to the Great American Songbook and his distinctive bel canto singing style helped endear him to new audiences, and he won the prestigious Grammy album of the year in 1995 for his MTV Unplugged: Tony Bennett release. His cross-genre, cross-generational appeal was made doubly clear with the release of two duets albums with Lady Gaga in the last decade of his life, both of which reached the top 10 of the Billboard 200.

Below, here are his 15 biggest singles on the Billboard charts.

Tony Bennett’s biggest hits are based on peak positions, and, in the event of a tie, by weeks on the chart. For songs released before 1958, peak positions are determined by the highest position among the three major predecessor pop charts – Best Sellers in Stores, Most Played by Jukeboxes or Most Played by DJs. For songs released after 1958, peak positions are from the Billboard Hot 100, which launched on Aug. 4, 1958.

Reporting by Trevor Anderson and Keith Caulfield.