Tony Bennett’s death brings the era of the great crooner to an end: He was Sinatra’s favorite singer who lit up Vegas and his songs were the soundtracks to millions of first dates

He was the singer revered by other lounge lizards as ‘The Guv’nor’ and one of the last living links to the era of classic crooners.

Tony Bennett’s death on Friday at the age of 96 marked the end of a remarkable seven-decade musical career, more than 70 albums and 19 Grammy awards.

The last of the great nightclub singers of the mid-20th century, Bennett was famed both for releasing classics and for hitting new standards like “I Left My Heart in San Francisco.”

Compared to his friend and mentor Frank Sinatra at the start of his career, Bennett first tried to distance himself, but ended up largely following the same path as other crooners of old – singing in nightclubs, on television and in the movies.

Later in life, he enjoyed a resurgence in popularity with younger audiences through a collection of duets with Lady Gaga – who became his friend and tour mate, along with other younger stars who rushed to collaborate with the singing legend.

Born in the Astoria neighborhood of Queens, New York in 1926, Anthony Dominick Benedetto first began performing at the age of 13, when he worked as a singing waiter at several neighborhood Italian restaurants.

After watching combat in the military in the latter stages of World War II in Europe, Benedetto toured with comedian Bob Hope, who was the first to suggest simplifying his name to Tony Bennett.

In 1950, Bennett signed with Columbia Records on a demo of the classic hit Boulevard of Broken Dreams.

Bennett’s powerful stage presence proved to be one of his greatest assets.

With a welcoming smile and smart suit, he sang with verve and smooth vibrato in a strong, clearly pronounced voice, which he kept in shape by training from the operatic Bel Canto tradition.

Beginning with his first big hit “Because of You” in 1951, Bennett sang dozens of chart-toppers including “Rags to Riches” and “Stranger in Paradise.”

His signature song “I Left My Heart in San Francisco” earned him his first two Grammy Awards in 1962, for Record Of The Year and Best Solo Vocal Performance, Male.

In a 1965 interview, Sinatra affirmed Bennett’s star status by calling him “the best singer in the business.”

“He turns me on when I look at him. He moves me. He’s the singer who conveys what the composer has in mind, and probably a little bit more,” said Sinatra.

Bennett later related the Guardian of Sinatra’s comment, “He was 10 years older than me and he was my idol, and when he announced I was his favorite singer, all his fans came to see me.” Since then I’ve been sold out.’

Although close friends with Sinatra, Bennett was never part of Sinatra’s “Rat Pack” crew, saying he didn’t have the stamina to party with the group of entertainers who had first gathered as Humphrey Bogart’s drinking buddies.

“I wasn’t in the Rat Pack,” Bennett once told the Express. ‘I had my singing and my painting, and with the hours they kept – whoa! – it’s a good thing I wasn’t in that scene.’

As the rock era began in the mid-1950s, Bennett moved from pop songs to jazz, collaborating with some of the top names in that genre and recording “Basie Swings, Bennett Sings” with the Count Basie Orchestra.

He drew his material from jazz and the work of writers such as Cole Porter, Johnny Mercer, George and Ira Gershwin and Richard Rodgers and Lorenz Hart.

But the British invasion led by The Beatles initially took its toll on the singer, whose music suddenly sounded strange and old-fashioned.

In 1970, studio executives pressured him to record an album of covers by The Beatles and other contemporary artists called “Tony Sings the Great Hits of Today!”

Bennett, who appeared on the album’s cover dressed unusually in wide-legged pants and a paisley ascot, described it as the low point of his career, saying that some songs made him “physically sick.”

He nearly died of a cocaine overdose in 1979 before sobering up and eventually reviving his career by returning to his roots as a classic crooner.

“When rap came on, or disco, whatever the new fashion was at the time, I wasn’t trying to find something that fit the style of the whole music scene,” Bennett told British culture magazine Clash.

“I just stayed myself and sang honestly and just tried to be honest with myself – never compromise, just do the best songs I could think of for the audience.

“And thankfully it paid off.”

By the early 1990s, Bennett—his style and appearance had changed little from the 1960s, save for more gray hair—appeared in music videos on MTV and sang warm-up at concerts by alternative rock giants such as Smashing Pumpkins and Porno for Pyros.

Proof that Bennett was back came in 1993 when he presented an award at the MTV Video Music Awards alongside the Red Hot Chili Peppers, who praised his cool factor and playfully sang part of “I Left My Heart in San Francisco.”

His career continued to grow and ten years later he released three successful albums of duets. On one, “Body and Soul,” he sang with Amy Winehouse in her last recording before she passed away in 2011 at age 27.

His bond with Winehouse was documented in the Oscar-nominated documentary “Amy,” in which Bennett patiently encouraged the insecure young singer during a performance.

Partners on his popular ‘Duet’ albums have ranged from former Beatle Paul McCartney and soul queen Aretha Franklin to country star Willie Nelson and U2’s Bono.

In 2014, at age 88, Bennett broke his own record as the oldest living artist with a No. 1 album on the Billboard 200 chart for “Cheek to Cheek,” his duet project with Lady Gaga.

He celebrated his 90th birthday with a star-studded concert at New York’s Radio City Music Hall, which was turned into a television special and album.

The title is taken from a song popularized by Bennett: ‘The Best Is Yet to Come.’

Bennett toured the United States and Europe in his last decade, playing a show in New Jersey on March 11, 2020 before pandemic lockdowns halted live performances.

Soon after, he revealed that he had been diagnosed with Alzheimer’s disease in 2016. He had kept his condition quiet for years and continued recording and performing despite the diagnosis.

His latest album, the 2021 release “Love for Sale,” featured duets with Lady Gaga on the title track, “Night and Day,” and other Porter songs.

Turning 95, Bennett played two more birthday concerts in August 2021, again at Radio City Music Hall, with Lady Gaga – shows that were billed as his farewell to New York and turned out to be his last live performances.

He subsequently canceled the rest of his 2021 tour dates on doctor’s orders.

“And let the music play as long as there’s a song to sing / And I’ll stay younger than spring,” he sang on the first of his farewell shows, in a rendition of his ballad “This Is All I Ask.”

“You were a good audience,” Bennett said before his encore. “I like this audience.”