Tony Bennett’s most iconic moments: from jazz classics, to collaborations with Lady Gaga and Amy Winehouse
One of the last great champions of the Great American Songbook, Tony Bennett, has died aged 96. The legendary vocalist, who forged a seven-decade career spanning jazz, big band and pop is best-known for hits such as 1951’s Because of You and Blue Velvet and 1962’s I Left My Heart in San Francisco, as well as his later collaborations with Lady Gaga, Amy Winehouse, and Aretha Franklin.
Born in Queens, New York, in 1926 Bennett – the son of two Italian immigrants, a grocer and a seamstress – grew up in poverty during the Great Depression, listening to the music of Louis Armstrong, Judy Garland, Bing Crosby, and Joe Venuti.
By the time he was 10, a young Bennett was already performing, and working around the city as a singing waiter in his early teens. Aged 18, his dreams of becoming a singer were put on hold as he was drafted into the US army and fought on the frontlines of World War II; while deployed he helped to liberate prisoners from Nazi concentration camps, and was demoted after dining with a friend, who was black, amid racial segregation in the army. His experiences would come to shape his pacifist and anti-war politics. "Anybody who thinks that war is romantic obviously hasn’t gone through one," he wrote in his 1998 memoir The Good Life.
After being discharged and returning to the US, Bennett returned to singing, waiting tables once more and recording under a series of names including Joe Bari and his birth name Anthony Benedetto. His first major breakthrough came after adopting the moniker he would use for the next seven decades: Tony Bennett. Following his 1951 demo of Boulevard of Broken Dreams, he inked a deal with Colombia, and a succession of his biggest hits followed. From here, he became a star.
Along with his Fifties classics, of course, Bennett was equally well known for mounting a remarkable comeback in the late Eighties to establish newfound relevance in a musical landscape that was fast changing in the wake of rock’n’roll, and his brilliantly surprising collaborations in more recent years.
As we remember a musical great, here are some of Tony Bennett’s most iconic moments and milestones.
The Fifties boom
Released in 1951, Because of You was Bennett’s first mega-hit, occupying the number one spot in the US Billboard charts for 10 weeks, and becoming a jukebox favourite. A lush, orchestral love song, it’s packed with swooning strings and trilling woodwind ,conducted by Percy Faith,
It was followed by Bennett’s take on Hank Williams’s honky-tonk country classic Cold, Cold Heart, the romantic croon of Blue Velvet, and the brass-laden big band swagger of Rags to Riches. Now a star in America Bennett’s popularity crossed the Atlantic when Stranger in Paradise – his promotional song for the Broadway musical Kismet – became a UK hit.
Steps into jazz
Having first made his name on classic crooning, 1955’s Cloud 7 – Bennett’s first studio album – was perhaps the first indication of jazz entering the fold. In the years following its release, he began collaborating with the celebrated jazz pianist Ralph Sharon for the first time; a rich artistic partnership which continued for almost fifty years. As well as collaborating on some of Bennett’s greatest songs, including Chicago, The Good Life, and I’ve Got the World on a String, the pair also worked together on 1962’s I Left My Heart in San Francisco; Bennett’s signature songs.
Bennett’s activism
Throughout Bennett’s incredible musical career, he was also a strident activist. In 1965, towards the end of the Jim Crow era, he marched alongside Martin Luther King in Selma; in the Eighties, he joined the likes of Muhammad Ali and Jane Fonda in Artists and Athletes Against Apartheid, lobbying for sanctions against the South African government. In 2013, meanwhile, Sir Paul McCartney was just one supporter of Bennett’s campaigning for tighter gun controls in the wake of the Newtown shootings. “I just believe that assault weapons, they were invented for war,” Bennett said, speaking at Capitol Hill. “They shouldn’t be on our streets here.”
When he turned 80, Bennett was honoured with a humanitarian award by the United Nations High Commissioner for Refugees, and was also inducted into the International Civil Rights Walk of Fame.
The Rock n’ Roll comeback
As rock’n’roll continued to sweep the Sixties, Bennett’s smooth, easy-listening fell further out of vogue; attempts to tap into the genre and reignite his career with more contemporary sounds and a number of best-forgotten Beatles covers fell flat, and soon enough, he found himself adrift and without a record label. The artist had financial issues, and struggled with drug addiction during this challenging period. "Look, I’m lost here," he told his sons following a near-fatal overdose in the late Seventies. "It seems like people don’t want to hear the music I make."
Bennett’s son Danny had plenty of ideas up his sleeve, and together they formulated a plan; by 1986 things were back on the up with an Oscar nomination for Bennett’s That’s Life theme song Life in a Looking Glass, and a newly inked deal with Colombia. Rather than attempting to drastically change Bennett’s image, he stuck with the same classic stylings, but pursued new audience, cameoing on The Simpsons, and inviting Elvis Costello and k.d. lang onto his celebrated appearance on MTV Unplugged.
The approach worked a treat. Steppin’ Out with My Baby became an unlikely MTV favourite, while Bennett’s similarly leftfield appearance at Glastonbury in 1998 during one of the festival’s earliest legends slots was a surprise standout, Bennett serenading an exceedingly muddy Worthy Farm in an immaculate suit.
The collaborations, from Amy Winehouse to Lady Gaga
From here, it was clear that Bennett was onto a winner; rather than diluting the essence of what made him a star in the first place, he set about bringing the beauty of the Great American Songbook to younger audiences. In 2006, the singer released his first Duets album – enlisting the likes of Celine Dion and George Michael – to belt out his classics, and in 2011 the number one charting Duets II followed. Opening with a duet with Lady Gaga, and also featuring soul legend Aretha Franklin, Carrie Underwood, Mariah Carey, Sheryl Crow, and Willie Nelson, it was a stroke of genius. Best of all, though, was Bennett’s duet with Amy Winehouse, Body and Soul, a jazz standard that was originally released in 1930. The final song Winehouse recorded before her death, aged just 27, it’s up there with his best.
In another first-class collaboration, Bennett forged a brilliantly unexpected friendship with the art pop singer Lady Gaga. The pair would go on to record two jazz albums together: 2014’s Cheek to Cheek, and 2021’s Love For Sale. The latter delved into Cole Porter’s big band classics, and also served as a sort of musical swan-song for Bennett – by then, 95-years-old, and struggling with Alzheimer’s disease – as he announced his well-earned retirement.
The friends also performed together at Bennett’s final concert One Last Time, two years ago. “Tony, we’re all so grateful to have witnessed your talent, your generosity, your creativity, your kindness, and your service through all the years," Gaga said at the moving farewell show.
