He was an integral part of the American cultural fabric, one of the music industry's shining lights, the Great American Songbook's biggest living champion and a generation-spanning one-of-a-kind talent whose iconic career stretched from radio days to the current streaming age. The death of Tony Bennett at age 96 marks the end of an era in both music and the nation at large; a legendary figure who transcended the decades with an unmatched voice and a burning passion for the music he performed.

A recipient of the Recording Academy's Lifetime Achievement Award in 2001, Bennett won 19 GRAMMYS among 41 nominations throughout his staggering career. His first two GRAMMYS came from his signature tune, "I Left My Heart in San Francisco," which won Best Solo Vocal Performance, Male and Record of the Year at the 1963 GRAMMYs (it was later inducted into the GRAMMY Hall of Fame in 1994). He most recently won a GRAMMY in 2022 for Traditional Best Pop Vocal Album for his Cole Porter tribute with Lady Gaga, Love For Sale.

"Tony Bennett was an iconic, once-in-a-generation voice in American music," said Harvey Mason jr, CEO of The Recording Academy. "A 19-time GRAMMY winner between 1962-2021, Tony's work has stood the test of time while being embraced universally by audiences and musicians across generations. We're honored to have celebrated Tony's GRAMMY moments, 2001 Lifetime Achievement Award, and 1994 GRAMMY Hall of Fame induction alongside him throughout his illustrious career. The world has lost an astounding talent, and he will be deeply missed."

In the wake of his passing, Bennett's monumental impact on music has left the medium's biggest names musing about his vast influence. "Without doubt the classiest singer, man, and performer you will ever see," said Elton John in an Instagram post. "He's irreplaceable. I loved and adored him." Billy Joel called Bennett "one of the most important interpreters of American popular song" in his own post, while fellow crooner Harry Connick Jr. wrote "You changed the world with your voice."

"From an early age, I've been blessed by now that I wanted to be involved in artistic endeavors," Bennett wrote in his 2012 memoir Life is a Gift. "Even though we were very poor, my parents placed a high value on the arts. I always wanted to sing and paint; I never had to ask, 'What am I going to do with my life?' I always knew."

Born Anthony Dominick Benedetto in Queens, New York, Bennett took early influence from his father, who was known to sing Italian folk songs; the crooner later credited his father (who died when he was 10) with inspiring his eventual career. Bennett's later service in World War II led to him to study at the American Theater Wing once stateside thanks to the G.I. Bill.

After a successful career as a club musician (where comedian Bob Hope bequeathed Bennett his shorter, angelized moniker), Columbia Records president Mitch Miller welcomed Bennett to his roster and in 1951, he released his first album Because of You. Of its eponymous single, Johnny Mathis later told GRAMMY.com it's the song he most personally associates with Tony. "His interpretation is so honest and it was very representative of the time," recalled Mathis of the track. "Because of You" was his first No. 1 hit — and in fitting form, it was also the last song he sang before his death.

Throughout his subsequent career, Bennett fiercely cherished the songs he sang, making hits of early recordings, from the bombastic "Rags to Riches" to the bittersweet "The Good Life." Though Bennett's catalog did include one dabble into modern pop hits with 1970's Tony Bennett Sings the Great Hits of Today!, his undying loyalty to his art manifested in his own response to the schlocky album: he later recalled throwing up the first time he heard it played back.

The consummate jazz virtuoso also embodied a steadfast determination to preserve and honor the Great American Songbook in his tribute albums. He recorded the music of everyone from friend and contemporary Ella Fitzegerald (1995's Here's to the Ladies), to several jazz greats on 2014's Cheek to Cheek, his first collaborative project with Lady Gaga.

Cheek to Cheek and the aforementioned Love for Sale — Bennett and Gaga's second LP together — both helped introduce Bennett to a new generation of listeners. In fact, Bennett reintroduced himself to fresh audiences multiple times during his career, whether his most recent bow with Gaga or in 1995 when his MTV Unplugged album won GRAMMYs for Best Traditional Pop Vocal Performance and the coveted Album of the Year.

The smooth romance of Bennett's voice also served as a motif for his catalog, a talent that The Voice himself, Frank Sinatra, first noticed. Lifelong friends until his death, Sinatra was famously quoted in a 1965 interview for Life Magazine saying, "For my money, Tony Bennett is the best singer in the business," a sentiment that cemented Bennett as an artist for all-time. (In the wake of his death, Sinatra's daughter Nancy called him "one of the most splendid people who ever lived.")

When it comes to vocal prowess alone, take for example "The Way You Look Tonight," the ultimate love song originally written in 1936 that Bennett first recorded in 1956, delivering multiple interpretations throughout his career. Elsewhere, it was during his '70s-era work with the pianist Bill Evans that showcased the singer's tender voice alongside Evans' tinkling piano, especially in the mournful  "Young and Foolish," on which he sings of a sunsetting of youth. 

"Overall, his absolute unrelenting commitment to excellence is at the forefront," musician and Bennett collaborator Gregg Field told GRAMMY.com last year. "In spite of decades of passing musical trends, Tony recognized greatness, and it is always that the next generation of artists that are attracted to his music."

But whether the songs he recorded were joyful or melancholy, Bennett's passion always shone through — and is ultimately what will make his legacy live on. "I encourage everyone to find their passion," he later wrote in Life is a Gift. "Work as hard as you can to follow your dreams; they will ultimately lead you to contentment in every aspect of your life. It's my goal at the end of the day to be able to lay my head on my pillow, knowing I've tried my best."

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