Tony Bennett dies: ‘The best singer in the business’ – how words from his idol Frank Sinatra changed his career

“For my money, Tony Bennett is the best singer in the business.”

Coming from Frank Sinatra himself, in an interview in 1965, there could be no higher compliment.

Sinatra was a huge influence on Bennett, who has died aged 96.

The pair had become firm friends and went on to perform together several times over the years.

Bennett was the younger singer – Sinatra died in May 1998 at the age of 82.

But as they both matured, Sinatra always continued to call Bennett “kid” – even into old age.

Bennett said his idol’s words in that 1965 article changed his career.

Two years earlier, a then 36-year-old Bennett had picked up his first Grammy for his signature song I Left My Heart In San Francisco.

In 2022, almost 60 years later, the pop and jazz singer was awarded his 20th, sharing the honour with his superstar collaborator Lady Gaga – at the tender age of 95.

During a career in entertainment spanning eight decades, Bennett was one of the last of America’s great crooners – one who achieved the rare feat of only seeming to grow in popularity in later life.

With more than 70 albums to his name, he is perhaps the only artist ever to have had new albums charting in the US in the 1950s, ’60s, ’70s, ’80s, ’90s, 2000s, 2010s and 2020s – and in 2014, he broke his own record as the oldest living artist to hit the top of the weekly Billboard 200 album chart.

Performing well into his 90s, even after being diagnosed with Alzheimer’s disease in 2016, Bennett was an entertainer beloved by all generations; Gaga was just one of the modern-day artists he collaborated with in later years.

Paul McCartney, John Legend, Christina Aguilera and Michael Buble, as well as Sinatra, all feature on the long list of others, and his 2011 duet with Amy Winehouse, Body And Soul, was the last song she recorded before her death.

“To me, life is a gift, and it’s a blessing to just be alive,” the singer once said.

It was a quote he became known for, the title of one of his memoirs, and one he used again when he went public about his illness in 2021.

“Life is a gift – even with Alzheimer’s,” was the message shared on his social media accounts in February 2021.

Later that year, he performed his final farewell shows.

Grief, war and discovery

Born Anthony Dominick Benedetto on 3 August 1926, in Queens in New York City, to parents John and Anna, the young Tony and his older brother and sister, John and Mary, were raised by their mother following his father’s death when he was aged just 10.

As a child, he loved to sing and paint, and his passions were nurtured at the High School of Industrial Arts in Manhattan.

As he grew older, he developed a love of music listening to artists such as Bing Crosby, Louis Armstrong and James ‘Jimmy’ Durante on the radio.

During his teenage years, Bennett sang while waiting tables, before enlisting in the army during the Second World War.

He served in the Battle of the Bulge – the last major German offensive campaign on the Western Front, launched in 1944 through the forested Ardennes region between Belgium and Luxembourg – and participated in the liberation of a concentration camp, according to his official website’s biography.

During his time in Europe, he performed with military bands and, following his return to America, he went on to have vocal studies at the American Theatre Wing School in New York.

The singer’s first nightclub performance came in 1946, alongside trombonist Tyree Glenn at the Shangri-La in Queens’ Astoria neighbourhood.

Three years later came his big break, when comedian Bob Hope noticed him working with actress and singer Pearl Bailey in Greenwich Village.

At the time, he was performing under the stage name of Joe Bari.

‘We’ll call you Tony Bennett’

Hope liked Bennett’s singing so much that he met him in his dressing room afterwards to ask him to perform with him at the city’s famed Paramount Theatre.

There was just one condition.

“But first he told me he didn’t care for my stage name and asked me what my real name was,” Bennett recalled. “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 Americanised name – the start of a wonderful career and a glorious adventure.”

Bennett’s first singles came in the 1950s, including chart-toppers Because Of You, Rags To Riches, and a remake of Hank Williams’ Cold, Cold Heart.

Dozens more singles followed and his voice took him around the world, selling millions of records and performing to sold-out venues – as well as to numerous stars and presidents.

He went on to release dozens of albums throughout the ’50s, ’60s and ’70s, but began to struggle with drug use as his style of music fell out of style.

Following a 10-year absence from the US album charts, he returned with The Art Of Excellence in 1986 and continued releasing music at pace in the 1990s, becoming an unlikely favourite of MTV.

Legendary duets add to his longevity

In 2001, well into his 70s, the singer was awarded a lifetime achievement award at the Grammys – but there was no sign of him slowing down.

He became known for his collaborations and his first modern-day duets album, Duets: An American Classic, was released in 2006, featuring performances with artists including McCartney, Elton John, Barbra Streisand and Bono.

After more than 50 years in the business, it was one of the bestselling records of his career.

Duets II came in 2011, featuring artists including Aretha Franklin and John Mayer, as well as Gaga and Winehouse.

Debuting at the top of the Billboard charts, it went on to win two Grammys, and his friendship with Gaga led to the release of their first collaborative album, Cheek To Cheek, in 2014.

Their second, Love For Sale, Bennett’s final album, came in 2021.

As well as his music, Bennett was also known for his painting, and had his work exhibited at galleries around the world.

He was even commissioned by the United Nations, painting one piece for the organisation’s 50th anniversary.

He was also the author of five books, including the New York Times bestseller Life Is A Gift: The Zen Of Bennett, published in 2012, and Just Getting Started, released in 2016.

Family and charitable legacy

A father of four, Bennett was married three times.

At his wedding to first wife Patricia Beech in 1952, some 2,000 female fans reportedly gathered outside the ceremony – dressed in black in mock mourning. The couple went on to have two sons, Danny and Dae, before they separated.

Bennett went on to marry actress Sandra Grant, with whom he had daughters Joanna and Antonia, and in 2007 married long-term partner Susan Crow, now Susan Benedetto.

In 1999, he founded Exploring the Arts with Susan, to help strengthen the role of the arts in public high school education in the US.

One of the organisation’s first projects was the establishment of the Frank Sinatra School of the Arts, a public high school set up in 2001 in Bennett’s hometown of Astoria, Queens.

The singer’s other charitable endeavours included helping to raise millions of dollars for the Juvenile Diabetes Foundation, which established a research fund in his name, and lending his artwork to the American Cancer Society’s annual holiday greeting cards to raise funds.

Along with his many gongs for his music, Bennett was also honoured with the Martin Luther King Center’s “salute to greatness” award for his efforts in fighting racial discrimination, after joining the activist in the Selma-to-Montgomery civil rights march in 1965.

The singer’s retirement from performing was announced in 2021, with his son Danny, also his manager, saying it was down to doctor’s orders due to the strain of travelling.

Performing a medley tribute to the man she described as “an incredible mentor, and friend, and father figure” at the Grammys in 2022, Gaga appeared emotional as she finished on stage. “I love you, Tony. We miss you.”

Following the singer’s death, the music industry mourns one of the last great performers of his generation.

For Bennett, life was a gift – and for millions of fans over the decades, it was a gift he gave right back.