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Tony Bennett Kept Coming Back Into Style

In the mid-1970s, Tony Bennett found himself in the most uncertain period of his life. “I’ve always tried to do the cream of the popular repertoire yet remain commercial,” he told the New Yorker in 1974, shortly after he’d left Columbia Records and was about to strike out with Improv, his own independent label. “Hanging out with good songs is the secret … I love singing too much to cheat the public. And I can’t ever lose that spirit by listening to the money boys, the Broadway wise guys who used to tell me, ‘If you don’t sing such-and-such, you’ll end up with a classy reputation and no bread in the bank.’ But if I lose that spirit, my feeling for music would run right out the window. It’s this obsolescence thing in America, where cars are made to break down and songs written to last two weeks. But good songs last forever, and I’ve come to learn that there’s a whole group out there in the audience who’s studying that with me.”

It was an accurate assessment and a prophetic one at that: Had he trusted outside noise instead of his gut, he would’ve missed out on his greatest hits, an enormous second life in his career, and a veritable collection of prolific collaborations, from Frank Sinatra, who once dubbed him “the best singer in the business,” to Lady Gaga, with whom he recorded a No. 1 album of these songs, 2014’s Cheek to Cheek, and enjoyed a fruitful creative partnership into his final days. To him, these pop and jazz gems were timeless, unimpeachable, his magnetic north — a principle he held even when favoring them meant risking financial ruin and irrelevance.

Bennett’s death this morning, at 96, comes two and a half years after his family revealed that he had been quietly living with Alzheimer’s disease since 2016. In spite of his neurological condition, he continued to perform and record with the gusto and ease that had earned him 19 Grammy Awards, two Emmys, Kennedy Center honors, and other notable distinctions in his lifetime — the vast majority of them earned after 1992’s Perfectly Frank, the album of Sinatra covers that revived his career. He had joined Gaga onstage multiple times on the road and at her Jazz & Piano musical at Las Vegas’ Park Theater as recently as 2019, toured in the early months of 2020, and reunited with her in the studio to record the follow-up to Cheek to Cheek, a collection of duets and a continuation of their shared affinity for the American Songbook, later last year. The AARP Magazine article announcing his illness detailed his decline as he drifted in and out of lucidity while working with Gaga on the album, all the more devastating as these once-familiar choruses and chord progressions only confused and overwhelmed him as they tried to record. Alzheimer’s attacks the brain cells that fuel and protect memory, a particularly cruel disease for an artist like Bennett, whose work is a testament to the power and durability of nostalgia. He not only relished in perfecting “I Left My Heart in San Francisco” and “They Can’t Take That Away From Me” as he grew as an artist over the years, but delighted in regaling his audiences with stories that brought them further into the music, and his love of it, that he so desperately wanted to share.

Anthony Dominick Benedetto was born on August 3, 1926, in Queens, to John Benedetto, an Italian grocer who immigrated to New York twenty years before his youngest son’s arrival, and Anna Benedetto (née Suraci), whose own Italian parents settled in the Lower East Side before the turn of the century. He was a creative kid, the sort who sang at school assemblies as he grew up in Astoria and soaked up his tap-dancer uncle’s stories about life on the road with the vaudeville circuit. He had his first brush with fame when he performed at the opening ceremony of the RFK Bridge (then Triborough) in 1936. Marching and singing alongside Mayor Fiorello La Guardia after the ribbon cutting was an “indelible” experience, as he told New York’s Chet Flippo in 1981: “Mayor La Guardia was patting me on the head and I saw everybody feeling so good and I just said, ‘I’d like to do this the rest of my life, make people feel that way.’”

His first gigs were close to home — stints as a singing waiter at Riccardo’s as a teenager; sitting in with trombonist Tyree Glenn at the Shangri-La for his first club appearance before he graduated from high school — but his musical dreams briefly paused in 1944 when he was drafted by the army and sent to Europe in the thick of World War II (though he sang in the armed forces’ special service band while away). Following his discharge in 1946, he enrolled at the American Theatre Wing thanks to the G.I. Bill, where he continued his musical studies and learned the bel canto technique he would later credit as the secret to his voice’s longevity. After a series of unsuccessful auditions, he eventually made it to the Greenwich Village Inn in 1949, where he joined Pearl Bailey’s ensemble as a singer and master of ceremonies. Bob Hope caught the show one night and was impressed by the young singer — but not Joe Bari, Bennett’s first stage name. The comedian came up with “Tony Bennett” by riffing on his given name and invited him to join him as his opening act uptown at the Paramount Theatre, and later on his subsequent tour.

The ’50s were kind to Bennett. He signed with Columbia Records in 1950, released the ornate, chart-topping ballad “Because of You,” and followed that with a cover of Hank Williams’s “Cold, Cold Heart,” another hit that was later heralded as the first pop-country crossover (though Williams called Bennett directly to voice his disapproval). He released nine albums — many of them featuring covers of Rodgers & Hammerstein show tunes and Gershwin standards — and hosted a nationally broadcast variety show on NBC. Life was sweet offstage, too, as he married Patricia Beech in 1952 and welcomed sons D’Andrea (who goes by Danny) in 1954 and Daegal (Dae) in 1955. But in 1962, Bennett reached a new threshold of fame when he joined Bing Crosby, the Rat Pack, and other velvet-voiced pros in the pantheon of American crooners with “I Left My Heart in San Francisco,” a love letter rife with longing for its hills and “golden sun.” The single garnered his first two Grammy awards and made him an international superstar. Cab drivers would sing it to him in midtown; the city of San Francisco eventually erected a statue in his honor. Comparisons to Sinatra mounted as his spotlight grew brighter, and the chairman of the board counted himself a vocal Bennett fan as he praised him in the pages of Life and onstage at any given opportunity. Bennett put out 14 albums before the close of the decade, even though listeners, especially younger ones, had begun to shift away from him and his tux-clad forebears towards rock and Motown. His sales declined, but his touring ramped up, and it took him away from home for long stretches — a sacrifice that ultimately led to his first porce, and second marriage. (He met Sandra Grant while filming The Oscar in 1965; the couple wed in 1971 and had two daughters, Joanna and Antonia.)

When he received pressure from Columbia to ditch the American Songbook in the ’70s and try recording hits by the Beatles and other contemporary acts, he did, but the records didn’t sell. Soon, it seemed that the aging crowds of Las Vegas were his only audience, and even they were dwindling. In 1979 he hit rock bottom: His second marriage broke up, and he landed in rehab following a cocaine overdose, after which he called his son Danny for help. The younger Bennett ditched his own musical aspirations to take on his father’s imploding career, and together, they started to slowly build on Bennett’s strengths while reinvigorating his image. Bennett got back in the studio, but instead of chasing fleeting trends for the sake of a payday, he doubled down on “hanging out with the good songs” by refreshing a few favorites with Perfectly Frank, his tribute to his old friend Sinatra, in 1992. The gamble paid off: It was his first gold record since “I Left My Heart in San Francisco” and demolished his unlucky streak when he took home his first Grammy award in 30 years for it in 1993. (Only two of Bennett’s 19 Grammys were awarded before Perfectly Frank, both for “San Francisco.”)

Bennett in 1958.Photo: Ray Fisher/Getty Images

His enduring voice, sparkling stage presence, and genuinely warm, approachable personality were well-known to his longtime fans, but Danny didn’t want to depend on their loyalty and expectations: He worked over the course of the ’80s to get his father in front of younger audiences by framing him as an elder statesman of pop that the cool kids of the ’90s wanted around. Suddenly, Bennett, cartoonified, was making a cameo on The Simpsons (as the first celebrity to voice his own image on the show), presenting at the MTV Video Music Awards alongside the Red Hot Chili Peppers, and filming his own MTV Unplugged special, which yielded a platinum album and another Grammy. He was the rare elder who got what the grandkids of his devoted fans were saying, but more important, he understood how to meet them where they were — and convert them.

Unlike many of his peers who spent their late years anchored exclusively in Las Vegas or retirement, Bennett wasn’t interested in resting on his laurels alone — or resting at all. In between tours and the occasional Vegas showcase, 2001’s Playin’ With My Friends: Bennett Sings the Blues brought a musical change-up and B.B. King, Stevie Wonder, Ray Charles, Billy Joel, Sheryl Crow, k.d. lang, and more into the studio; 2006’s Duets: An American Classic, released just after Bennett’s 80th birthday, featured collaborations with Barbra Streisand, Paul McCartney, Elton John, Celine Dion, James Taylor, the Chicks, Juanes, and John Legend, among others. With 2011’s Duets II, Bennett courted some of the most venerated voices in pop and rising stars of the moment, from Aretha Franklin and Mariah Carey to Amy Winehouse, Carrie Underwood, and Lady Gaga. Duets II was a triumph and broke new personal records for Bennett: The album was his first to hit No. 1 on the Billboard 200 albums chart, which made him the oldest artist to ever achieve the feat, and “Body and Soul,” his duet with Winehouse, landed on the Hot 100 chart at No. 87 — his first song to do so in decades.

When he reunited with Gaga for 2014’s Cheek to Cheek, Bennett had long since proven the naysayers wrong: People still hadn’t tired of the Gershwins’ languid ballads and Porter’s clever flirtations, and new fans embraced Bennett and Gaga’s camaraderie as they hammed it up in the studio and delighted in reinterpreting these classics with her vibrant flair and his elegant cool. Cheek to Cheek was another validating chart-topper for Bennett: The album debuted at No. 1.

“She helped me, and I helped her by doing Cheek to Cheek,” Bennett told Vulture in 2015. “Through her telling her audience how much she likes me, all of them became fans of mine, all these young teenagers. On the other hand, by her singing these beautiful songs on the album, the audience I have, all of them said, ‘God, I never knew she sang that wonderfully.’ So we both helped one another.”

Gaga’s Jazz & Piano residency in Las Vegas leaned heavily on Cheek to Cheek, and Bennett joined her there a few times, where he sang and joked like a proud uncle who was eager to show off his thriving protégé as she took over the family business. He was given a rare gift in the twilight of his life, in that he not only passed his torch but entrusted his legacy to an artist and friend who loved these songs as much as he did.

Bennett will be missed for myriad reasons — his talent, of course, but also his charm, his kindness, and his resilience in the face of a mercurial industry that can shift its loyalties and machinations before the end of a song. In his 1981 interview with New York, he was adamant that these American Songbook tunes would last beyond him: “I think that 100 years from now they will become America’s classical music … those songs will live.” Thanks to Bennett and those following his lead, they will.

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