Tony Bennett was a monument, but never a relic. He collaborated with the history of pop music, from Rosemary Clooney and Count Basie to Amy Winehouse and Lady Gaga. As a symbol, he represented old, glamorous show biz and unparalleled longevity. As a singer, he soundtracked eight decades with his warm, inviting vocal quality. As his once-soaring voice aged, it developed a friendly gravel that delivered each note with expressive bravado.

Bennett will be remembered alongside his signature song "I Left My Heart in San Francisco," but his legacy will stay forever linked with New York City. His voice was that first sight at the skyline, followed by a cocktail in a Manhattan hotel bar. Frank Sinatra called him the greatest popular vocalist in the world. 

Anthony Dominick Benedetto was born in Astoria, Queens, New York on Aug. 3, 1926, to Italian immigrant parents. He studied singing and painting at the High School of Industrial Art before being drafted into World War II in 1944. After returning from conflict in the European theater, Benedetto sang with the Armed Forces band. 

An early, successful television appearance led to a gig opening for performances at a Greenwich Village club. There, he caught the attention of Bob Hope. Hope rechristened the young singer "Tony Bennett," and a star was born. A contract with Columbia Records followed, as did a string of hits like "Cold, Cold Heart," "Because of You," and "Rags to Riches."

Bennett's career had many peaks and valleys. He left Columbia in 1971 after a series of unremarkable singles, bristling as the label insisted his sound changed with the world around him. After a six-year stint managing his own label, Improv, Bennett was soon also without a manager. Plagued by the I.R.S. and personal issues, Tony was then joined by son Danny Bennett, who assumed the management of his father's career, revitalizing the singer for the start of a new decade. The '80s saw a revitalization, with television appearances on "The David Letterman Show" and the MTV Video Music Awards. 

The youth-oriented network brought a new audience to Tony Bennett's music. While the singer continued to rack up Grammys for his traditional vocal albums, "MTV Unplugged" provided an unprecedented generational bridge, allowing this new crowd to hear not only Bennett's songs but also the stories behind them. He released 70 albums over the course of his career.

At 96, Tony Bennett still had not overstayed his welcome. Although he was diagnosed with Alzheimer's disease in 2016, Bennett continued to perform regularly. His final public appearance was in August 2021, when he performed at Radio City Music Hall with Lady Gaga. 

The legendary crooner passed away on July 21, 2023, at his home in New York City. Tony Bennett is survived by his wife Susan Benedetto, his two sons, Danny and Dae Bennett, his daughters Johanna Bennett and Antonia Bennett, and his nine grandchildren.