The following is from LIFE’s special tribute issue to Tony Bennett, available at newsstands and here online.

The show biz ladder had few rungs lower than Anthony Dominick Benedetto’s gig at Riccardo’s, the Italian restaurant in his hometown, Astoria, Queens, New York, where, at 16, he worked as a singing waiter. But the artist the world came to know as Tony Bennett worked the dining room the same way he would the Copa or Carnegie Hall—he gave it his all. “We’d get a request from a customer and then I’d run back into the kitchen to work out the arrangements,” he recalled in his 1998 memoir, The Good Life. “I really cut my teeth as a performer at that job.”

His dreams then did not extend beyond the beckoning lights of nearby Manhattan. “When you’d see this big city,” he told the New York Times decades later, “you’d say, ‘Boy, wouldn’t it be great to become famous in that great city there?’” Tony Bennett and his music would conquer territories far beyond the island of Manhattan. “If America is a song,” Anthony Hopkins said in the narration of a 2007 PBS American Masters, “Tony Bennett is its singer.”

By the time of his death on July 21, 2023, at age 96, Bennett was more than a national treasure. “I Left My Heart in San Francisco,” was his signature. But he put his heart into every song and the bel canto—the “beautiful music”—of his voice was heard around the world. “When it comes to heart,” critic (and Good Life coauthor) Will Friedwald wrote, “Bennett is a virtuoso.”

He leaves a legacy greater than his 50 million albums sold, his 90-plus singles, his 19 Grammy Awards amassed in a hit-making career that began in 1950 and found him still at it, releasing acclaimed albums, performing and even touring, well into his nineties. Long running acts of a younger generation like Bob Dylan and the Rolling Stones will have to remain on the road another full decade and more to match Bennett’s longevity. Collaborations with music giants from Duke Ellington and Count Basie to 21st-century stars such as Amy Winehouse and Lady Gaga earned accolades in genres and music epochs that span the history of popular music from the post–World War II era to today.

The son of Italian immigrants—his father, Giovanni, emigrated at age 11; his mother, Anna, crossed the ocean in utero and was born in America—Bennett came from a long line of singers on his father’s side. “Singing,” he wrote, “is in my blood.” A mobbed-in-the-streets pop idol at 25, his star dimmed during the reigns of Elvis and the Beatles. But it was secured, thanks in part to “San Francisco,” the 1962 smash that kept his music in the air throughout a decade that saw the careers of contemporaries go into near permanent eclipse. At the same time, Bennett, a passionate and lifelong civil rights advocate, earned an honored place in the annals of the movement when he marched alongside Martin Luther King in 1964.

Beset in the 1970s by drug and money problems, he engineered a startling career resurgence in the following decades. “Tony Bennett has not just bridged the generation gap,” the New York Times wrote of his Grammy-winning 1994 MTV Unplugged performance, “he has demolished it.”

Indeed, his dimpled grin, like his gleaming green eyes, Roman nose and nobly tailored tuxedos, became as familiar to new generations of fans as his exultant performances, his devotion to the Great American Songbook classics and his unwavering optimism. “I’ve been singing for 60 years,” Bennett exclaimed at the 2005 Monterey Jazz Festival. “If I get lucky enough I’d like to sing for another 60 years. Beautiful!”

Through most of  his later decades, Bennett enjoyed the good life indeed. After two otherwise failed marriages—the first produced two sons, D’Andrea (Danny) and Daegel (Dae, for short); the second, daughters Joanna and Antonia—he wed his long-time companion Susan Crow, a former New York City social studies teacher turned artist manager, in 2007. He devoted himself to another lifelong passion, painting, and to his and his wife’s arts education foundation. In a kind of monument to Bennett’s modesty, the New York City public school for performing and visual arts that he and his wife founded in his native Astoria is named not for Bennett but for his own musical hero, Frank Sinatra. In February 2021, his wife and sons revealed that Bennett had Alzheimer’s, the progressive, debilitating form of dementia that had first been diagnosed in 2016. While ravaging so much of life that he held dear, the disease had, almost miraculously it seemed, left his gift intact, allowing him to perform in concert right up until he gave his final public performance in August 2021.  Thereafter he continued to perform at home, encouraged by his family and caregivers for singing’s therapeutic value. “There’s a lot about him that I miss,” Susan told AARP magazine in 2021. “Because he’s not the old Tony anymore.” After a pause to steady her voice, she added, “But when he sings, he’s the old Tony.”

Here is a selection of photos from LIFE’s special tribute issue to Tony Bennett.

Simon Ritter/Redferns/Getty

Tony Bennett with his first wife, Patricia, in their Tenafly, N.J. home, 1957.

David McLane/NY Daily News Archive/Getty

Tony Bennett performed during Johnny Carson’s debut as host of The Tonight Show on Oct. 1, 1962.

NBCU Photo Bank/Getty

Tony Bennett was out with Frank Sinatra after a performance in Miami, 1965.

John Dominis/The LIFE Picture Collection/Shutterstock

Tony Bennett and Duke Ellington performed together at the Grammy Awards, 1966.

NBCU Photo Bank/Getty

Tony Bennett, circa 1970.

Michael Ochs Archives/Getty

Tony Bennett’s output of recordings was already voluminous when he posed for this photo in 1970; over the course of his career he would release 90 albums.

Photo by Michael Ochs Archives/Getty Images

Tony Bennett with second wife Sandra and daughter Joanna at the London Zoo, 1972.

Everett Collection Historical/Alamy

Tony Bennett played with his daughter Joanna, then six years old, at his apartment on Central Park South in New York City, 1977.

Richard Corkery/NY Daily News Archive/Getty

Diana Krall and Tony Bennett performed at the 2018 CMA Country Christmas on Sept. 27, 2018 in Nashville.

Jason Kempin/Getty

Tony Bennett performed with Billy Joel at Madison Square Garden In New York City on April 12, 2019.

Kevin Mazur/Getty

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