Tony Bennett, who has died aged 96, made a high art out of being the very best kind of saloon-bar singer – not only in the good-humoured optimism of his big, expansive sound, or his passionate gratitude for life’s lucky breaks and glimpsed beauties, but also in an unquenchable appetite for sharing good songs, whether with 10 people or 10,000.
Frank Sinatra used to call Bennett “the best singer in the business”, an accolade that would frequently turn up in the younger man’s publicity, though a more forthright tribute from the same source (“that kid’s got four sets of balls”) generally did not. Bennett’s artistry and power to stir the heart were qualities a world away from the cliched perception of the Vegas crooner in a tuxedo. During the rock-dominated 1960s and 70s, Bennett was easy to caricature. You only had to pretend to loosen a tie, casually throw an imaginary microphone from hand to hand, and exhale “the loveliness of Paris” in tones somewhere between Sinatra’s and the club style of Vic Reeves.
Closer listening to Bennett’s smoky baritone revealed a different story. His performances often sounded like thanksgivings – for the breaks he’d had, and for his conviction that the good in the world outstripped the bad. This curiously worldly innocence was at the core of his enduring appeal. Bennett’s records (including Because of You and a version of the country singer Hank Williams’s Cold, Cold Heart) topped the charts in 1951 before the arrival of rock’n’roll. His most celebrated later hits included his signature song, I Left My Heart in San Francisco, The Good Life (both 1962) and Who Can I Turn To? (1964). Bennett won 19 Grammy awards and was estimated to have sold more than 50m records worldwide.
He was also an accomplished painter and produced a book of his visual art, What My Heart Has Seen (1996). His autobiography, published in 1998, was entitled The Good Life – Bennett knew only too well how ambiguous a notion that could be, having narrowly survived a cocaine overdose and fought off bankruptcy during his troubled middle years. He raised millions of dollars for charities and publicly associated himself with liberal causes. In an interview with the singer in 2002, Simon Hattenstone wrote in the Guardian that Bennett had “done all the classic showbiz stuff, snorted coke with the best of ’em, made out with the younger women, broken bread with the mafia – and somehow come out with his innocence, his idealism, intact”.
Born Anthony Dominick Benedetto in the Astoria district of Queens, New York, he was the son of John, a grocer from southern Italy, and Anna (nee Suraci), a seamstress. His father died when Bennett was 10 and Anna worked all hours to support her three children. Watching her struggle, Bennett made up his mind to be successful enough for his mother’s trials to end. His Uncle Dick, a tap dancer, provided an early glimpse of showbusiness, and Bennett was passionate about both singing and painting by the time he attended the School of Industrial Art (now the High School of Art and Design) in Manhattan.
He took bellboy jobs before becoming a singing waiter in a restaurant. Bennett sang with army bands during the second world war, but he was demoted and assigned to gravedigging for fraternising on Thanksgiving night with a black soldier who had been a schoolfriend. Twenty years after that episode, Bennett was marching in Alabama with Martin Luther King. He was moved to become a pacifist following combat in Europe in 1945, an experience he described as “a front-row seat in hell”.
After demobilisation, Bennett took vocal classes in the bel canto style at the American Theatre Wing school (a teacher there suggested he try imitating the phrasing of jazz instrumentalists) and he began singing in nightclubs from 1946 under the stage name of Joe Bari. The comedian Bob Hope hired him in 1949, but, disliking the stage name, told him: “We’ll call you Tony Bennett.”
Bennett worked in New York at the Paramount theatre in Hope’s popular show, which soon needed police barricades to hold back the singer’s teenage fans. When he married Patricia Beech in 1952, crowds of young women showed up outside the ceremony, dressed as if in mourning.
Bennett became one of the biggest vocal draws in the US, with three No 1 hits – Because of You, Cold, Cold Heart (both 1951) and Rags to Riches (1953). His single Stranger in Paradise, from the Broadway musical Kismet, brought him a No 1 in the UK in 1955 but the arrival of rock’n’roll made it Bennett’s first and last Top 10 single in the UK, and he had only one more in the US, when In the Middle of an Island reached No 9 in 1957.
Bennett needed to adapt. Unlike Sinatra or Bing Crosby, he had not worked with the swing big-bands, a learning curve alongside expert instrumentalists that could sharpen technique and fill a singer with fresh ideas. But in 1957 he began a long working relationship with the London-born jazz pianist and arranger Ralph Sharon, who edged him toward a jazzier repertoire. Bennett’s 1957 album The Beat of My Heart was made with help from the jazz musicians Herbie Mann, Art Blakey and Jo Jones among others; it was followed by Basie Swings, Bennett Sings (1958) and In Person! (1959) with Count Basie’s big band.
Bennett began 1962 as a man at the top of his game. Sharon, who was friendly with the songwriters George Cory and Douglass Cross, introduced him to their song I Left My Heart in San Francisco. Bennett recorded it as a B-side to Once Upon a Time; it went gold, won two Grammys and secured a June concert for the singer at Carnegie Hall. He also sang on the first broadcast of The Tonight Show Starring Johnny Carson that October. But that month, the Beatles released their debut single, Love Me Do, and by spring 1964 it was No 1 in the US.
Along with many other singers of his kind, Bennett found that his sales went into steady decline. He tried an unsuccessful detour into acting before, in 1969, the Columbia Records boss Clive Davis persuaded him to make an album of 60s pop hits including the Beatles’ Eleanor Rigby. The cover art portrayed him in flares and a psychedelic tie, and Bennett was so intimidated by his unsuitability for material he was not yet ready to appreciate that he threw up during the recordings. He later said it reminded him of his mother being forced to make cheap dresses for money.
Bennett left Columbia and worked for smaller jazz labels during the next decade. He performed with the big bands of Woody Herman, Buddy Rich and Duke Ellington, and in 1975 made a duo album for the Fantasy label with one of modern jazz’s most lyrical pianists, Bill Evans. What might have seemed like an unlikely partnership between the cerebral Evans and the heart-on-sleeve popular performer worked remarkably well, with Bennett’s account of Evans’ famous Waltz for Debby revealing an inspired grasp of the art of jazz-inflected vocal interpretation and interplay. Two years later, the pair reconvened for Together Again on Bennett’s own shortlived Improv label.
Improv’s bankruptcy, the failure of Bennett’s second marriage, to Sandra Grant, his cocaine habit and the decline of his gigs outside Las Vegas brought darkening days for the singer in the 70s, capped by the tax authorities trying to seize his Los Angeles house. In 1979 he almost died of an overdose, and appealed for help to the sons from his first marriage, Danny (born D’Andrea) and Dae (born Daegal). Danny became his father’s manager and relaunched his career on a smaller scale through the college and theatre circuit. Sharon was back on piano, and Bennett returned to Columbia but with creative control. With the album The Art of Excellence (1986), produced by Danny, the 60-year-old vocalist’s career was about to boom again.
In the 90s he paid tributes to Sinatra and Fred Astaire, on the albums Perfectly Frank and Steppin’ Out, respectively, and also recorded homages to Billie Holiday (Tony Bennett on Holiday) and Duke Ellington (Bennett Sings Ellington: Hot and Cool). Through his work with kd lang and Elvis Costello on MTV, he reconnected with a young audience. He even played at Glastonbury in 1998, with the organisers laying out a path of hay bales so he wouldn’t get his silk suit muddy on the way to the stage.
On Playin’ With My Friends: Bennett Sings the Blues (2001), he recorded a memorable series of duets with lang, Ray Charles, Sheryl Crow, Billy Joel, Diana Krall, BB King, Bonnie Raitt and Stevie Wonder.
For his 80th birthday in 2006, Bennett released Duets: An American Classic, featuring performances with Paul McCartney, Elton John, Barbra Streisand and Bono, and five years later came Duets II, with another glitzy cast including Aretha Franklin, Lady Gaga – and Amy Winehouse, with whom he shared a memorable Body and Soul in March 2011.
The old star sounded warmly respectful, and the young one unfurled all her formidable jazz-improviser’s credentials. After Winehouse’s death in July that year, Bennett opined that if she had lived she might have matched the achievements of Holiday or Dinah Washington. Duets II made No 1 on the Billboard album chart, making Bennett the only 85-year-old artist to have hit that spot.
In 2012, his book of philosophical musings, Life Is a Gift, was published. The 2014 album Tony Bennett & Lady Gaga: Cheek to Cheek was another Billboard chart-topper, and the following year he won a Grammy for a tribute album to Jerome Kern.
The Empire State Building was specially illuminated for Bennett’s 90th birthday in 2016 – and that year Stevie Wonder, Bob Dylan, Lady Gaga and more performed on an NBC primetime special, Tony Bennett Celebrates 90: The Best Is Yet to Come. The Butler Institute of American Art in Ohio (where Bennett’s Homage to Hockney is part of a permanent collection) presented its Two Painters exhibition, showing Bennett’s Tuscan landscapes, still lifes and portraits alongside watercolourist Charles Reid’s work. In November 2017, the Library of Congress made him the first non-composer to win the Gershwin prize.
Bennett worked into his later years – because a new audience was there for him, and because the money funded his charitable work, including the Frank Sinatra School of the Arts, which he had founded in 2001. He painted every day for as long as he was able. “You paint with nature out in the field and you realise how magnificent being alive is,” Bennett enthused to Hattenstone in 2002. “Most people just walk past it. I used to walk past it. Each day now, because of my age, I just look at it and cherish it. If people could only grasp how wonderful it is to be part of this.” A diagnosis of Alzheimer’s in 2016 did not dim this view, with Bennett stating on Twitter: “Life is a gift – even with Alzheimer’s.”
His final live performances were with Lady Gaga in 2021, at Radio City Music Hall, New York.
Bennett’s first two marriages ended in divorce. In 2007 he married Susan Crow, who survives him, as do his sons, and two daughters, Joanna and Antonia, from his second marriage.
• Tony Bennett (Anthony Dominick Benedetto), singer, born 3 August 1926; died 21 July 2023
