Tony Bennett, legendary New York pop and jazz singer

Born August 3, 1926;

Died: July 21, 2023

Tony Bennett, who has died at the age of 96, was a unique figure in the world of pop music – a star who was embraced by successive generations right up until the end of his life. By staying true to his ethos of picking the very best material, he managed to come back, and be relevant once more, each time his style of music had fallen out of fashion. 

During an astonishing seven-decade career, Bennett amassed 20 Grammy Awards and a mountain of hits – among them Rags to Riches, Because of You, his signature song I Left My Heart in San Francisco and The Good Life - and attracted fans from the worlds of pop and jazz music. While other, younger, singers came along and dipped a toe in the Great American Songbook as a token nod of respect, Bennett championed such Great American songwriters as Jerome Kern, the Gerswhins and Cole Porter right through his career, to the point where, once Frank Sinatra and Ella Fitzgerald had died in the late 1990s, he was effectively the custodian of those classic standards.

He certainly saw himself in that role, and in 2014 he told The Herald that he felt a responsibility to keep singing those songs. He may already have been well into his eighties when he took to the stage of the Glasgow Royal Concert Hall in September of that year, but, over the course of a non-stop, 75-minute performance, he romped through a programme of no fewer than 26 songs, without pausing for anything more than the briefest chat and acknowledgment of the massive outpouring of affection for him from the packed venue. 

The bottom line was that he loved to sing – and he loved to make people happy. He cited Louis Armstrong as his primary inspiration as a singer, and explained how he shared Armstrong’s outlook. “His whole life he just wanted to make people feel good and have fun. He loved what he was doing so much that it never became old-fashioned.”

Born Anthony Dominick Benedetto in 1926, Bennett first heard Armstrong’s recordings as a youngster growing up in the Queens borough of New York.  Before his discovery of of jazz, however, it was his father’s Caruso records which introduced him to the art of singing, and in particular to the “bel canto” style, which explains his graceful way with a song and his elegant phrasing.

Bennett lost his father when he was only ten years old, and his mother found herself with three young children and no money. This was 1936, the height of the Great Depression. Music was initially a distraction from the sadness of his father’s death, but it soon offered a practical escape route out of poverty. Bennett, whose first job was as a singing waiter, said: “I went into showbusiness to stop my mother from working - she was making a penny a dress sewing in a sweat shop to put food on the table for her children.”

Bennett was drafted into the US Army in November 1944 and was assigned as a replacement infantryman to the 255th Infantry Regiment of the 63rd Infantry Division, a unit filling in after the Battle of the Bulge. He moved across France and into Germany, and in March 1945, he joined the front line. As the German army was pushed back, Bennett and his company experienced bitter winter fighting and eventually helped liberate a concentration camp. The young singer’s combat experience made him a lifelong pacifist. 

Bennett stayed in Germany as part of the occupying force, assigned to an informal Special Services band unit which entertained nearby American forces. Upon his return to the States in 1946, he took advantage of the government’s GI Bill of Rights, which provided returning soldiers with free college education. Bennett went to the American Theater wing where he learned what he described as “the rudiments of the entertainment world”, and where the notion of never compromising on quality was instilled in him.

One of his tutors had an office on 52nd Street, then the epicentre of jazz in New York. Her advice proved life-changing: “Don’t imitate singers, because you’ll just be one of the chorus if you do that. Imitate musicians, find out what they like.” Among the names plastered across the nightclub awnings visible from her window were Art Tatum, Stan Getz, Erroll Garner, Billie Holiday, Count Basie and Miles Davis. 

She told the young Bennett: “Look at these awnings, find out who you like, and then get influenced by listening to how they phrase and what they’re doing, and then you’ll find your style that way.” Bennett zoned in on piano giant Art Tatum, “because he made a production out of a song, which wasn’t done in those days at all. He’d change the tempo, he’d go to the keys and make a song come alive and end up telling a story, rather than just singing a straight line for everyone to smoothly dance to.” Later, Bennett said, “Stan Getz knocked me out because he had this honey sound, and so I put the two together and arrived at a style that way”.

In 1950, Bennett handed in a demo record to Columbia and was signed on the spot. The following year, his recording Boulevard of Broken Dreams began a run of hits which also included Because of You, Cold, Cold Heart, Blue Velvet and Stranger in Paradise. By the late 1950s, rock ‘n’ roll was dominating the pop charts and Bennett’s popularity began to flag, only to be reignited, in 1962, by his recording of I Left My Heart in San Francisco, a massive hit which paved the way for a string of grown-up, bittersweet ballads such as I Wanna Be Around, The Good Life and The Shadow of Your Smile.

By the end of the 1960s, Bennett, like many of his contemporaries, was considered old hat and was under pressure to get with the contemporary pop music - rock. The album Tony Sings the Great Hits of Today, instigated by his label, made him feel “physically sick” and he parted company from Columbia Records in 1972, not to return until 1986. 

This prolonged period out of the pop limelight produced some highly acclaimed jazz albums on his own Improv label – notably two albums of much admired duets with pianist Bill Evans and two sublime volumes of the Rodgers & Hart Songbook with the Ruby Braff/George Barnes Quartet; intimate, cult recordings which are among the very best vocal works in all jazz and which highlight Bennett’s admiration and respect for the some of the most eloquent lyrics in the Great American Songbook. 

By the late 1970s, however, Bennett was at the lowest point in his professional and personal lives: his second marriage broke down, he had developed a cocaine habit and he owed money to the tax man. A near fatal cocaine overdose was the catalyst for him to ask for help from his sons from his first marriage.

Under the astute management of his son Danny, who helped to shift his father’s image away from old Vegas, brought him back to New York, sorted out his finances and negotiated a deal with Columbia which gave him artistic control, Bennett made a triumphant comeback to the pop scene in the late 1980s. He never fell from popular favour again thanks partly to the fact that he became seen as an elder statesman who almost singlehandedly represented the era of Frank Sinatra and Ella Fitzgerald, and also because he regularly collaborated with the “in” singers of the moment, everyone from kd lang to Lady Gaga – performing standards from his beloved Great American Songbook, and making them appeal to a new, young audience. His 1995 Grammy-winning MTV Unplugged record and his famous, show-stopping, appearance at Glastonbury in 1998 sum up his successful reinvention as someone who, as the New York Times put it, didn’t “just bridge the generation gap; he demolished it”. 

Bennett told The Herald that the most satisfying aspect of his later success was that it allowed him to be exactly the kind of singer he wanted to be – singing jazz with his quartet and creating an intimate atmosphere even in the largest venue. “I like working that way,” he says. “To clarify my whole premise: I don’t want to be the biggest. I’d rather be one of the best.” The Silver Lining, a tribute to Jerome Kern on which he duetted with the pianist Bill Charlap, was released in late 2015 and confirms categorically that he achieved his ambition. It, plus Love For Sale, his 2019 collaboration with Lady Gaga, earned him the last two of his 20 Grammy awards.

Not only was Bennett revered as a singer, he was also a well-regarded and prolific artist; painting had been his other passion since childhood. He was also passionate about the civil rights movement, with which he was actively involved in in the turbulent 1960s, and for which he was recognised on the International Civil Rights Walk of Fame. Earlier, during his wartime service, he had been demoted and reassigned after breaking the army’s segregation rules and dining with a black friend. In his later life, he was additionally known for his charitable work, which included the establishment of the Frank Sinatra School of the Arts in Queens, New York – a school for artistically gifted teenagers. 

Bennett is survived by his third wife, Susan, and by his four children from his first two marriages.

Alison Kerr