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.
Bennett performs with Lady Gaga
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.
Pic: AP
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.
Pic: AP
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.
Pic: AP
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.
Flight tracking data shows extensive movement of US military aircraft towards the Middle East in recent days, including via the UK.
Fifty-two US military planes were spotted flying over the eastern Mediterranean towards the Middle East between Monday and Thursday.
That includes at least 25 that passed through Chania airport, on the Greek island of Crete – an eight-fold increase in the rate of arrivals compared to the first half of June.
The movement of military equipment comes as the US considers whether to assist Israel in its conflict with Iran.
Of the 52 planes spotted over the eastern Mediterranean, 32 are used for transporting troops or cargo, 18 are used for mid-air refuelling and two are reconnaissance planes.
Forbes McKenzie, founder of McKenzie Intelligence, says that this indicates “the build-up of warfighting capability, which was not [in the region] before”.
Sky’s data does not include fighter jets, which typically fly without publicly revealing their location.
An air traffic control recording from Wednesday suggests that F-22 Raptors are among the planes being sent across the Atlantic, while 12 F-35 fighter jets were photographed travelling from the UK to the Middle East on Wednesday.
A US air tanker seen flying over Suffolk, accompanied by F-35 jets. Pic: Instagram/g.lockaviation
Many US military planes are passing through UK
A growing number of US Air Force planes have been passing through the UK in recent days.
Analysis of flight tracking data at three key air bases in the UK shows 63 US military flights landing between 16 and 19 June – more than double the rate of arrivals earlier in June.
On Thursday, Sky News filmed three US military C-17A Globemaster III transport aircraft and a C-130 Hercules military cargo plane arriving at Glasgow’s Prestwick Airport.
Flight tracking data shows that one of the planes arrived from an air base in Jordan, having earlier travelled there from Germany.
What does Israel need from US?
Israeli Prime Minister Benjamin Netanyahu said on 15 March that his country’s aim is to remove “two existential threats – the nuclear threat and the ballistic missile threat”.
Israel says that Iran is attempting to develop a nuclear bomb, though Iran says its nuclear facilities are only for civilian energy purposes.
A US intelligence assessment in March concluded that Iran is not building a nuclear weapon. President Trump dismissed the assessment on Tuesday, saying: “I think they were very close to having one.”
Forbes McKenzie says the Americans have a “very similar inventory of weapons systems” to the Israelis, “but of course, they also have the much-talked-about GBU-57”.
A GBU-57, or the Massive Ordnance Penetrator bomb, at Whiteman Air Base in Missouri in 2023. File pic: US Air Force via AP
The GBU-57 is a 30,000lb bomb – the largest non-nuclear bomb in existence. Mr McKenzie explains that it is “specifically designed to destroy targets which are very deep underground”.
Experts say it is the only weapon with any chance of destroying Iran’s main enrichment site, which is located underneath a mountain at Fordow.
Map showing the Fordow enrichment plant
Air-to-air refuelling could allow Israel to carry larger bombs
Among the dozens of US aircraft that Sky News tracked over the eastern Mediterranean in recent days, more than a third (18 planes) were designed for air-to-air refuelling.
“These are crucial because Israel is the best part of a thousand miles away from Iran,” says Sky News military analyst Sean Bell.
“Most military fighter jets would struggle to do those 2,000-mile round trips and have enough combat fuel.”
The ability to refuel mid-flight would also allow Israeli planes to carry heavier munitions, including bunker-buster bombs necessary to destroy the tunnels and silos where Iran stores many of its missiles.
Satellite imagery captured on 15 June shows the aftermath of Israeli strikes on a missile facility near the western city of Kermanshah, which destroyed at least 12 buildings at the site.
Seven of the 12 destroyed buildings at Kermanshah missile facility, Iran, 15 June 2025. Pic: Maxar
At least four tunnel entrances were also damaged in the strikes, two of which can be seen in the image below.
Damaged tunnel entrances at Kermanshah missile facility, Iran, 15 June 2025. Pic: Maxar
Writing for Jane’s Defence Weekly, military analyst Jeremy Binnie says it looked like the tunnels were “targeted using guided munitions coming in at angles, not destroyed from above using penetrator bombs, raising the possibility that the damage can be cleared, enabling any [missile launchers] trapped inside to deploy”.
“This might reflect the limited payloads that Israeli aircraft can carry to Iran,” he adds.
Penetrator bombs, also known as bunker-busters, are much heavier than other types of munitions and as a result require more fuel to transport.
Israel does not have the latest generation of refuelling aircraft, Mr Binnie says, meaning it is likely to struggle to deploy a significant number of penetrator bombs.
Israel has struck most of Iran’s western missile bases
Even without direct US assistance, the Israeli air force has managed to inflict significant damage on Iran’s missile launch capacity.
Sky News has confirmed Israeli strikes on at least five of Iran’s six known missile bases in the west of the country.
On Monday, the IDF said that its strategy of targeting western launch sites had forced Iran to rely on its bases in the centre of the country, such as Isfahan – around 1,500km (930 miles) from Israel.
Among Iran’s most advanced weapons are three types of solid-fuelled rockets fitted with highly manoeuvrable warheads: Fattah-1, Kheibar Shekan and Haj Qassam.
The use of solid fuel makes these missiles easy to transport and fast to launch, while their manoeuvrable warheads make them better at evading Israeli air defences. However, none of them are capable of striking Israel from such a distance.
Iran is known to possess five types of missile capable of travelling more than 1,500km, but only one of these uses solid fuel – the Sijjil-1.
On 18 June, Iran claimed to have used this missile against Israel for the first time.
Iran’s missiles have caused significant damage
Iran’s missile attacks have killed at least 24 people in Israel and wounded hundreds, according to the Israeli foreign ministry.
The number of air raid alerts in Israel has topped 1,000 every day since the start of hostilities, reaching a peak of 3,024 on 15 June.
Iran has managed to strike some government buildings, including one in the city of Haifa on Friday.
And on 13 June, in Iran’s most notable targeting success so far, an Iranian missile impacted on or near the headquarters of Israel’s defence ministry in Tel Aviv.
Most of the Iranian strikes verified by Sky News, however, have hit civilian targets. These include residential buildings, a school and a university.
On Thursday, one missile hit the Soroka Medical Center in Beersheba, southern Israel’s main hospital. More than 70 people were injured, according to Israel’s health ministry.
Iranian foreign minister Abbas Araghchi said that Iran had struck a nearby technology park containing an IDF cyber defence training centre, and that the “blast wave caused superficial damage to a small section” of the hospital.
However, the technology park is in fact 1.2km away from where the missile struck.
Photos of the hospital show evidence of a direct hit, with a large section of one building’s roof completely destroyed.
A general view of Soroka hospital following a missile strike from Iran on Israel.
Pic: Reuters
Iran successfully struck the technology park on Friday, though its missile fell in an open area, causing damage to a nearby residential building but no casualties.
Israel has killed much of Iran’s military leadership
It’s not clear exactly how many people Israel’s strikes in Iran have killed, or how many are civilians. Estimates by human rights groups of the total number of fatalities exceed 600.
What is clear is that among the military personnel killed are many key figures in the Iranian armed forces, including the military’s chief of staff, deputy head of intelligence and deputy head of operations.
Key figures in the powerful Revolutionary Guard have also been killed, including the militia’s commander-in-chief, its aerospace force commander and its air defences commander.
On Thursday, Israeli Prime Minister Benjamin Netanyahu said that US assistance was not necessary for Israel to win the war.
“We will achieve all our objectives and hit all of their nuclear facilities,” he said. “We have the capability to do that.”
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How close is Iran to producing a nuclear weapon?
Forbes McKenzie says that while Israel has secured significant victories in the war so far, “they only have so much fuel, they only have so many munitions”.
“The Americans have an ability to keep up the pace of operations that the Israelis have started, and they’re able to do it for an indefinite period of time.”
Additional reporting by data journalist Joely Santa Cruz and OSINT producers Freya Gibson, Lina-Sirine Zitout and Sam Doak.
The Data and Forensics team is a multi-skilled unit dedicated to providing transparent journalism from Sky News. We gather, analyse and visualise data to tell data-driven stories. We combine traditional reporting skills with advanced analysis of satellite images, social media and other open source information. Through multimedia storytelling we aim to better explain the world while also showing how our journalism is done.
This is the most significant statement from the US president in days, though it still keeps everyone guessing.
In a message conveyed through his press secretary, he is giving diplomacy up to two weeks to work.
“Based on the fact that there’s a substantial chance of negotiations that may or may not take place with Iran in the near future, I will make my decision whether or not to go within the next two weeks,” Karoline Leavitt quoted him as saying.
It is not clear what “whether or not to go” entails.
Israel-Iran conflict: Latest updates
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Trump: Iran ‘weeks away’ from nuclear weapon
We know that he has been given a spectrum of different military options by his generals and we know that the Israelis are pressuring him to use American B2 bombers with their bunker-busting bombs to destroy Iran’s nuclear facility at Fodow.
The Israelis are encouraging no delay. But against that, he is weighing up many risks, both military and political.
Militarily, it is not clear how successful a bunker-busting strike on Fordow would be.
Experts have suggested it would require several of the massive bombs, which have never been used in combat before, to be dropped on the site.
It is not as simple as one clean strike and job done.
Politically, the president is under significant pressure domestically not to get involved in Iran.
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MAGA civil war breaks out over Iran
Within his own MAGA coalition – influencers, politicians and media personalities are lining up in criticism of involvement in the conflict.
One of those leading the criticism, his former chief strategist Steve Bannon, who maintains huge influence, was seen entering the White House on Thursday.
His press secretary reiterated to us that the president always wants to give diplomacy a chance and she confirmed that his Middle East envoy Steve Witkoff has spoken to the Iranian foreign minister Abbas Araghchi.
Steve Bannon, seen recently at a conservative event in Maryland, is against US involvement in Iran. Pic: AP
European leaders, including the UK foreign secretary David Lammy, who is in Washington, are meeting Mr Araghchi in Geneva on Friday.
The two-week window – assuming it lasts that long – also gives space to better prepare for any strike and mitigate against some of the other risks of US involvement.
Read more from Sky News:
Is Trump losing his MAGA support?
Gantz defends conflict with Iran
‘Love Trump’ says Israeli minister
There are 40,000 troops in bases across the Middle East. It takes time to increase security at these bases or to move non-essential personnel out. It also takes time to move strategic military assets into the region.
The USS Nimitz aircraft carrier and its support vessels were redeployed from the Indo-Pacific on Monday. Their last known position was the Strait of Malacca two days ago.
The Nimitz Carrier Group will overlap with the USS Carl Vinson group which was deployed to the Middle East in March.
The potential two-week window also allows for more time for a ‘day after’ plan, given that the Israeli strategy appears to be regime change from within.
Since the Israeli action in Iran began last week, the worst-case scenario of mass casualties in Israel from Iranian attacks has not materialised.
The president is said to be surprised and encouraged by this. “Israel has exceeded a lot of people’s expectations in their abilities,” press secretary Karoline Leavitt said.
The Israeli success, the absence of a mass casualty event in Israel, and the lack of any sustained counterattack by Iranian proxies in the region remove reservations that previous presidents have had about taking on Iran.
That said, sources have told Sky News that the president is determined that the diplomatic solution should be given a chance despite current pessimism over the chances of success.
A critical two weeks ahead.
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