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 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 Grammy for 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 20 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, Keith Caulfield and Paul Grein.
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"Congratulations to Someone"
Chart Peak: No. 20, March 1953
Songwriters: Roy Alfred, Al Frisch
Notes: This is the first of two songs on this list co-written by Frisch.
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"Firefly"
Chart Peak: No. 20, October 1958
Songwriters: Cy Coleman, Carolyn Leigh
Notes: This is the first of two songs on this list co-written by Coleman.
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"I Left My Heart in San Francisco"
Chart Peak: No. 19, October 1962
Songwriters: George Cory, Doug Cross
Grammy Awards: record of the year, best solo vocal performance, male, Grammy Hall of Fame
Notes: This was the only song that Bennett sang unaccompanied on his 2006 album Duets: An American Classic.
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"The Autumn Waltz"
Chart Peak: No. 18 in November 1956
Songwriters: Cy Coleman, Bob Hilliard
Notes: This is the first of two songs on this list that was written or co-written by Hilliard. The B-side of this single didn’t chart as high, but is better-known — “Just in Time” from the Broadway show Bells Are Ringing.
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"The Good Life"
Chart Peak: No. 18, June 1963
Songwriters: Sacha Distel, Jack Reardon
Notes: Billy Joel teamed with Bennett to sing this song on Duets: An American Classic.
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"Solitaire”
Chart Peak: No. 17, November 1951
Songwriters: Renee Borek, King Guion, Carl Nutter
Notes: This was the B-side of Bennett’s hit, “Blue Velvet.”
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“Have a Good Time”
Chart Peak: No. 16, September 1952
Songwriters: Boudleaux Bryant, Felice Bryant
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“Blue Velvet”
Chart Peak: No. 16, November 1951
Songwriters: Lee Morris, Bernie Wayne
Notes: A cover version of this song by Bobby Vinton topped the Hot 100 for three weeks in September/October 1963. k.d. lang teamed with Bennett to sing this song on his album Duets II, which topped the Billboard 200 in October 2011.
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"Can You Find It in Your Heart"
Chart Peak: No. 16, June 1956
Songwriters: Robert Allen, Al Stillman
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“Here in My Heart”
Chart Peak: No. 15, August 1952
Songwriters: Bill Borrelli, Pat Genaro, Lou Levinson
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“I Wanna Be Around”
Chart Peak: No. 14, March 1963
Songwriters: Johnny Mercer, Sadie Vimmerstedt
Grammy Nominations: record of the year, best vocal performance, male
Notes: Bono teamed with Bennett to sing this song on Duets: An American Classic. The Johnny Mercer Award, the top honor presented by the Songwriters Hall of Fame, was named after the songwriter whose many accomplishments include winning four Oscars for best original song.
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“I Won’t Cry Anymore”
Chart Peak: No. 12, August 1951
Songwriters: Al Frisch, Fred Wise
Notes: This was the B-side of Bennett’s hit “Because of You.”
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"Cinnamon Sinner”
Chart Peak: No. 8, September 1954
Songwriter: Lincoln Chase
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“There’ll Be No Teardrops Here Tonight”
Chart Peak: No. 7, April 1954
Songwriter: Hank Williams
Notes: This was Bennett’s second top 10 hit written by the country legend.
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"From the Candy Store on the Corner to the Chapel on the Hill"
Chart Peak: No. 11, September 1956
Songwriter: Bob Hilliard
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“In the Middle of an Island”
Chart Peak: No. 9, September 1957
Songwriters: Nick Acquaviva, Ted Varnick
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“Stranger in Paradise”
Chart Peak: No. 2, February 1954
Songwriters: George Forrest, Robert White
Notes: This gorgeous ballad was taken from the Broadway musical, Kismet. Andrea Bocelli teamed with Bennett to sing it on Duets II.
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"Cold, Cold Heart”
Chart Peak: No. 1 (six weeks), November-December 1951
Songwriter: Hank Williams
Notes: Williams’ version topped a forerunner of Billboard’s Hot Country Songs chart in May 1951. Tim McGraw teamed with Bennett to sing this song on Duets: An American Classic.
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“Rags to Riches”
Chart Peak: No. 1 (eight weeks), November 1953 to January 1954
Songwriters: Richard Adler, Jerry Ross
Notes: Elton John teamed with Bennett to sing this song on Duets: An American Classic.
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“Because of You”
Chart Peak: No. 1 (10 weeks), September-October 1951
Songwriters: Arthur Hammerstein/Dudley Wilkinson
Notes: k.d. lang teamed with Bennett to sing this song on Duets: An American Classic.