Tony Bennett Was a Master at Bridging Generational Divides

Tony Bennett, a standard bearer of the American Songbook whose resilient career stretched from duetting with Judy Garland to Lady Gaga, died on July 21 at the age of 96. His publicist, Sylvia Weiner, confirmed his death to the Associated Press. He had been diagnosed with Alzheimer’s disease in 2016.

Bennett started singing jazz standards as a teenage waiter and never stopped, despite persistent pleas from producers and record executives to diversify his repertoire. While the sound of music shifted dramatically from decade to decade, Bennett remained staunchly committed to bringing his laid-back, amiable interpretation of jazz to each new generation. He packed concert halls during Beatlemania, endeared himself to the MTV crowd, and seamlessly adapted to the streaming era.

“Back in the ‘60s, I was told I had to change my music for the kids to accept me. Yet through the years, every age responds to my singing, even though I haven’t changed a thing,” he wrote in his 2012 memoir, Life is a Gift: The Zen of Bennett.

Bennett’s expressive, enveloping singing voice never wavered and miraculously, he achieved his greatest commercial success in his last dozen years, some half a century after he recorded his signature song, “I Left My Heart in San Francisco.” In 2011, at 85 years old, he scored his first number one on the Billboard 200 with Duets II, making him the oldest artist ever to top the charts. Three years later, he broke his own record when Cheek to Cheek with Lady Gaga topped the charts and went gold. “I tell Tony every day that he saved my life,” Lady Gaga said in a 2014 interview.

Bennett gave a significant amount of his time and money to causes like civil rights, arts education and cancer research. He marched in Selma, won the United Nations’ Humanitarian Award in 2006, and founded the Frank Sinatra School of the Arts in his hometown neighborhood of Astoria, Queens. He was also an avid painter whose works have been exhibited in museums including the National Portrait Gallery.

For many, Bennett was synonymous with class, craftsmanship, perseverance and American excellence. He was one of the greats of the Greatest Generation; a reverent interpreter and revitalizer of a golden era of American songwriting. He died a Kennedy Center honoree, an NEA Jazz Master, a 19-time Grammy winner; he sang for every American president from Dwight Eisenhower to Barack Obama. “For my money, Tony Bennett is the best singer in the business,” Frank Sinatra said several times.

Scrappy Great Depression-era roots

Bennett was born Anthony Dominick Benedetto on August 3, 1926, as the grandson of Italian immigrants. He grew up in Astoria, where his mother, Anna Suraci, and father, John Benedetto, who were first cousins, ran a grocery store.

Bennett’s father was often ill and died of congestive heart failure and pneumonia when Bennett was 10, leaving him and his two siblings in the care of his mother and relatives at the height of the Great Depression. After selling the store, his mother worked as a seamstress in the garment district and sewed dresses by night, earning a penny a dress.

Despite their meager means, Bennett’s mother was uncompromising toward her craft, refusing to work on dresses she considered shoddy. “We were desperate for money, but she couldn’t bring herself to do something she felt was beneath her,” Bennett wrote in Life Is a Gift. “She became my inspiration for insisting on singing only quality songs.”

Bennett’s vocal talents were clear from an early age. At 10, he sang at the opening of the Triborough Bridge alongside Mayor Fiorello LaGuardia. He attended the High School of Industrial Arts, where he studied music and art, but dropped out at 16 to help his mother stay afloat financially. He took on odd jobs throughout the city—elevator operator, usher, library page—while also putting his talents to work as a singing waiter.

“I would go back to the kitchen where two Irish waiters would teach me the song, then go out into the dining room and perform for an extra tip,” he told biographer David Evanier.

Sketching in the foxholes

By this point, the United States had entered World War II. When Bennett turned 18 in 1944, he was promptly drafted and sent to the Western Front, where he arrived just after the infamous Battle of the Bulge. While Bennett avoided the brunt of the bloodshed, he nonetheless risked his life many times while fighting across German territory in the dead of winter. He saw many friends die and distracted himself by sketching while in foxholes. In 1945, he was in a company that liberated part of the Dachau concentration camp in Landsberg am Lech, Bavaria.

“It was a terrifying, demoralizing experience for me,” Bennett wrote in his 1998 autobiography, The Good Life. “I saw things no human being should ever have to see.”

When the war ended, Bennett stayed in Germany and briefly sang in a military band. In 1946, he was honorably discharged and returned home, taking advantage of the GI Bill to attend the newly formed American Theater Wing, which fostered the careers of luminaries including James Earl Jones and Angela Lansbury. While Bennett never seriously pursued acting, he did learn how to imbue his singing performances with narrative suspense and emotion, setting him apart from an eager generation of crooners.

Bennett’s big break arrived in 1949 while toiling away on the New York club circuit. While he was performing under the moniker of Joe Bari, comedian Bob Hope caught one of his sets in Greenwich Village. Impressed, Hope gave Bennett a life-changing opportunity on one condition—that he change his name. “‘Come on kid, you’re going to come to the Paramount and sing with me,’” Bennett recalled Hope saying. “But first he told me he didn’t care for my stage name and asked me what my real name was. I told him, ‘My name is Anthony Dominick Benedetto,’ and he said, ‘We’ll call you Tony Bennett.’ And that’s how it happened. A new Americanized name—the start of a wonderful career and a glorious adventure.”

“I almost fainted,” Bennett said of the encounter.

‘Idol of the Girls’

The name stuck, and so did Bennett’s popularity. Bennett’s immediate rise was a rags-to-riches tale that seemed to spin right out of a movie montage: Hope took Bennett on tour, which led the 23-year-old to sign with Columbia. There, he landed a string of hits that showed off his semi-operatic chops and romantic sensibilities, from “Because of You” to “Cold, Cold Heart” to “Blue Velvet” to “Stranger in Paradise.” His songs dominated on jukeboxes in ice cream parlors and bars across the country, making him the epitome of a pop star before rock ‘n’ roll would crash into America within the next few years. TIME called him “Idol of the Girls” in 1952; that year, when he married Patricia Ann Beech, 2,000 girls in black veils came to mourn outside his wedding ceremony.

Bennett arrived on the national stage nearly fully formed as a singer. What he lacked in range he made up for with an impeccable sense of swing, compelling lyrical interpretation and a genial warmth that put audiences at ease. He performed at the Paramount seven times a day, developing an unparalleled work ethic and learning how to modulate his performances for different age groups. Before long, he was performing at some of the most prestigious rooms in the country, from the Copacabana to Caesar’s Palace to Carnegie Hall.

Bennett’s attention to detail and professionalism also gained him the respect of some of the greatest artists in America. He sang with the jazz greats of a previous generation—from Duke Ellington to Ella Fitzgerald to Count Basie—and became friends with Frank Sinatra, who consistently sang his praises and even called him “the best singer in the business.” In 1968, Judy Garland called him “the epitome of what entertainers were put on earth for.”

The biggest solo hit of Bennett’s career was conceived of as little more than an afterthought. While on tour in 1962, Bennett’s longtime pianist Ralph Sharon found sheet music to a song about San Francisco in a clothing drawer and suggested they play it while in the Bay Area. When Bennett eventually recorded it, Columbia put it on the B-side of a single, thinking it would be little more than a regional crowd-pleaser.

Instead, “I Left My Heart in San Francisco” remained on the charts for 25 months, earning Bennett his first two Grammys. It went gold, became an official anthem of San Francisco, and in 2018 was selected for the National Recording Registry by the Library of Congress.

“Recent reports from Vietnam say it is the song of this war,” a 1968 Billboard article read. “Soldiers sing along with Tony’s record on a jukebox or record player or on the radio… By the time Tony’s voice reaches the line, ‘When I come home to you, San Francisco,’ every soldier is too overcome with emotion to continue.”

‘It seemed like the world was turning upside down’

While Bennett had towering successes, he was also fighting vicious battles behind the scenes. Rock ‘n’ roll had arrived and steamrolled the music business, making many crooners obsolete; Bennett’s own records began to slip down the charts, much to the chagrin of his record label, Columbia. Bennett’s prime nemesis of the era was Clive Davis, the powerful industry veteran who took over Columbia in 1967 and pushed Bennett to record more modern songs. (“His repertory was dated, and the public wasn’t buying it,” Davis would later write.) Bennett, for his part, was horrified that a non-musician like Davis would be put in charge of a music label. When he finally agreed to record modern pop songs for the 1970 album that would become Tony Bennett Sings the Great Hits of Today, he actually vomited after one session.

“It seemed like the world was turning upside down,” Bennett wrote in Life is a Gift. “When the bean counters take control, things go down the tubes.”

In the following years, Bennett’s life spiraled out of control: He divorced his first wife, developed a drug addiction to cocaine, started a failing independent record label, entered into an unhappy second marriage with Sandra Grant and sank deeply into debt. “I had an ax over my head. I was spending more than I was making, on advertising, publicity and all,” he told the New York Times in 1999.

In 1979, Bennett nearly died from a cocaine overdose after being told that the IRS was about to seize his house. “I overindulged in drugs and passed out in the bathtub. I could have died and after that I realized I had to get my life in order,” he wrote in Life is a Gift.

A new generation of fans

In this time of crisis, Bennett turned to someone close to him to right the ship: his elder son, Danny. The then-25-year-old became his financial adviser and immediately implemented a spending budget and forged a plan to pay back his father’s IRS debt. It was also Danny’s commercial strategy that fueled Bennett’s resurgence: He put an emphasis on courting younger audiences, believing his father’s appeal was timeless.

Bennett then started playing colleges and small theaters, and making regular appearances on Late Night With David Letterman, which skewed toward a collegiate crowd. In 1990, he was the first celebrity to appear as an animated version of themselves on The Simpsons. He appeared on Muppets Tonight, was profiled in the iconoclastic Spin Magazine and played benefit concerts at alternative rock radio stations around the country.

In 1994, Bennett performed on the zeitgeisty show MTV Unplugged just months after Nirvana had performed on the program. The ensuing live album, which included cameos from younger stars like k.d. Lang and Elvis Costello, went platinum and won album of the year at the Grammys. “Tony Bennett has not just bridged the generation gap; he has demolished it,” the New York Times wrote in a review.

When Bennett hit 70 in 1996, his popularity continued to ascend. Live By Request, an A&E concert show he created, drew more than 1.5 million calls for song requests during its first episode and won an Emmy. Bennett made cameo appearances in Analyze This and Bruce Almighty; Saturday Night Live even paid tribute to him with a recurring impersonation by Alec Baldwin.

In the ‘00s, Bennett turned his focus to collaborations, becoming an elder statesman for the American songbook tradition and the keeper of its flame. Across three Billboard-charting duet albums, he recorded standards with a stunning array of pop stars across genres and generations—from Paul McCartney to Christina Aguilera to Barbra Streisand to Amy Winehouse.

He also famously took Lady Gaga under his wing at a time when she was struggling with physical pain, criticism of her music and industry fatigue. “I couldn’t sleep. I felt dead,” she said in 2014. “And then I spent a lot of time with Tony. He wanted nothing but my friendship and my voice.” Together, they recorded the number one album Cheek to Cheek and toured across the world to the tune of $15.3 million.

In 2004, he even landed his first composing credit, for writing the words to “All for You” to a Django Reinhardt melody.

Bennett’s efforts have meant that classic compositions written some 80 years ago, including by Harold Arlen, Cole Porter, and Lerner and Loewe, are now recognizable to a new generation. “In the polluted sea of irony, bad faith and grotesque attitudinizing that pop music has become, he is a rock of integrity,” Stephen Holden wrote in the New York Times in 2006.

Bennett’s career continued to thrive during his golden years, consistently performing at live events, selling paintings for thousands of dollars, and being honored with various awards, including the Grammy Lifetime Achievement Award in 2011.

He also earned praise for his work supporting social justice and the arts. In 2001, he founded the Frank Sinatra School of the Arts, a performing arts school which still boasts extremely high graduation rates, a wide array of artistic programming, and strong racial and socioeconomic diversity.

“My friend Tony Bennett has been there for my people early on, earlier than most, and has stayed the course ever since,” Stevie Wonder said while presenting him with the Billboard Century Award in 2006. “He has helped demand the social, economic and civil rights of every American.”

Bennett barely slowed toward the end of his life despite his Alzheimer’s diagnosis: even when names, places and recent memories eluded him, he still was able to perform in concert and nail performances of songs he had first learned sixty years ago, bringing cool-but-accessible joie de vivre to every song. In 2021, he broke a Guinness World Record in becoming the oldest person to release an album of new material, at 95 years and 60 days. “The public deserves nothing but the best so don’t give them any junk,” Bennett told TIME in 2012. “Don’t give them anything that’s going to make a quick buck and be forgotten, don’t do anything unless it’s top quality.”