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Tony Bennett, a singer’s singer whose steadfast allegiance to the Great American Songbook would connect him with multiple generations of diverse talent – Pearl Bailey, Count Basie, Amy Winehouse and Lady Gaga — died on Friday morning (July 21) at his home in New York according to a statement from his management company. He was 96-years-old.

The singer was diagnosed with Alzheimer’s Disease in 2016 and in 2021 he announced that he was retiring from touring and performing after one last show in August of that year with good friend and avowed superfan Gaga at Radio City Music Hall entitled “One Last Time.”

Bennett had a continuous recording career from 1950 to 2014 that would see him release more than 60 albums, 44 of which would chart on the Billboard 200, win 16 Grammy Awards, and include a signature song in “I Left My Heart in San Francisco.” Over the last 25 years, Bennett thrived as the primary connection between modern pop and the music of the first half of the 20^th century that came from Tin Pan Alley, Broadway shows and movies. Sticking to his style as he recorded with Gaga, Elvis Costello, k.d. lang and Winehouse, Bennett became a paragon of multi-generational cool starting in the early 1990s as he toured the world and, in 2011 at the age of 85, had his first No. 1 album with Duets II.

A student of the bel canto style of singing, Bennett developed his own voice by going to the jazz clubs on New York’s 52^nd Street and listening to musicians such as saxophonist Charlie Parker and pianist Art Tatum. (A performance Tatum once gave of “Danny Boy” affected Bennett to the point that he named his first song Danny). He was following the advice of his voice teacher, Miriam Spier, who advised him that the only way to stand out is to emulate instrumentalists rather than other singers.

“I prefer the way the jazz artists work, and this is one of the things I have learned over the years from guys like (cornetist) Bobby Hackett,” Bennett told Billboard in 1968. “The way you feel it is the way it comes out, and it’s never the same way twice. That’s the way I like to sing — as if I just picked up the lead sheet for the first time.”

Bennett would stick to his guns about songs and his interpretations, even when it meant leaving Columbia Records after 23 years and forming his own label, Improv Records. Similarly, his output in the 1980s slowed as he resisted following trends, the payoff coming in the ‘90s when he paid tribute to the work of Fred Astaire, Frank Sinatra and Billie Holiday and exposed a 21^st century generation to the music he cut his teeth on.

“How does a singer get good performances out of himself,” Bennett wrote in a 1968 issue of Billboard. “Through dedication to his own talent. Through his wish to communicate with the listener in the audience. Through the songs he personally believes in.”

Born Antonio Dominick Benedetto in Long Island City, N.Y., on Aug. 3, 1926, Bennett started singing when he was 5, learning Irish songs from locals in his Astoria neighborhood and earn pennies and nickels for his performances.

Bennett’s father was ill most of the singer’s life, dying when Bennett was 10. His mother became a seamstress and, to contribute to the household of three children, Bennett, whose inspirations were Bing Crosby, Louis Armstrong and Jimmy Durante, started singing in a tavern for $15 a week. At 16, he working as an usher at Ditmars Theater, worked as a singing waiter in a couple of local clubs and sang on weekends at a club in Paterson, N.J.

His goal, however, was to become a commercial artist after finishing studies at the High School of Industrial Arts in Manhattan. (He would be an avid visual artist his entire life, using his given name for his oil paintings). Bennett joined the Army and was stationed in Germany where he sang with Army bands.

After his discharge from the service, Bennett studied drama, diction and music theory at the American Theatre Wing. He started a singing in nightclubs in 1946, using the name Joe Barri.

He was opening for Pearl Bailey in 1949 at the Greenwich Village Inn when Bob Hope heard him and offered him an opening slot on his show at the Paramount Theatre. No fan of the name Joe Bari, Hope decided the singer’s birth name was too long for a marquee and suggested the Americanized “Tony Bennett.” Around that time he appeared on Arthur Godfrey’s Talent Scouts TV show, coming in second place to Rosemary Clooney.

“I went to the Paramount Theater with Louis Prima,” Bennett told Billboard in 2006 when he received the Billboard Century Award. We had to do seven shows a day — start at 10 a.m. and go until 10 p.m. Sinatra did the same. It was tough.”

While on the road with Hope, a demo recording he had done of “Boulevard of Broken Dreams” led to Columbia Records bringing him in for a session. Bennett recorded four songs, “Boulevard” among them, on April 17, 1950; 10 days later “Boulevard of Broken Dreams” was released and would go to No. 1 for 10 weeks.

Bennett landed 12 top 20 singles between 1951 and 1954: “Because of You,” “Cold, Cold Heart” and “Rags to Riches” went to No. 1; “Stranger in Paradise” peaked at No. 2.

An early sign that he would work without attention to genre was “Cold, Cold Heart,” the first pop recording of a Hank Williams song. Jerry Wexler, while working at Billboard prior to joining Atlantic Records, played Williams’ version for Columbia A&R executive Mitch Miller, who brought the song to Bennett.

The recording exposed Williams to a pop audience for the first time, starting atrend that would become Bennett’s forte: In his first 18 years of making records, Billboard credited Bennett with introducing nearly 60 songs, helping establish writers such as Cy Coleman and Charles deForest. And he did so on his own terms, singing pop on singles and turning to jazz for his albums, recording with Art Blakey, Zoot Sims, Count Basie, Bill Evans, Frank Wess and other leading jazz artists.

His 1957 album The Beat of My Heart was jazz interpretations of standards given heavily percussive arrangements andfeaturing the drummer backed by Blakey, Jo Jones and Chico Hamilton. He wasalso the first male pop singer to work with Basie, releasing In Person with Count Basie and His Orchestra in 1959.

“The Count’s attitude became my philosophy — economy of keep it simple, keep it swingin’,” Bennett once said.

Bennett landed four top 20 hits on the Hot 100 in 1956, “In the Middle of an Island” charting highest, No. 9 in 1957. Miller, in a 1968 interview with Billboard, said a hit for Columbia at the time was anything that sold at least 150,000copies. Initial pressings of all of Bennett’s record were 200,000, to which Miller said “we’ve never overestimated.”

Still, entering the 1960s, he was in a top 20 dry spell, which may have owed to him avoiding the urging of Columbia brass to try more pop-oriented material.

“In the American Theatre Wing they insisted on no compromise,” Bennett told Billboard in 1968. “Mitch Miller actually understood where I was coming from though he was frustrated with me. I try to just never compromise. Not to be stubborn, but I don’t like to insult the audience.”

In 1961, during a stay in Hot Springs, Ark., Bennett’s pianist since 1956, Ralph Sharon, brought to Bennett a song written by his friends George Cory and Douglass Cross. Sharon suggested he sing it during his December 1961 run at the Venetian Room at the Fairmont Hotel in San Francisco.

“He played it for me and I liked it right away,” Bennett told Billboard. “It had been around and nothing had happened. I sang it at the Fairmont Hotel, but didn’t record it until six months later.”

“I Left My Heart in San Francisco” peaked at No. 19 in 1961, but the album I Left My Heart in San Francisco would enjoy 149 weeks on the Billboard 200, peaking at No. 5.

“Before I recorded ‘San Francisco,’ the trend of the music business was moving away from me,” Bennett told Billboard in 1968. “I was advised to try all sorts of tricks and gimmicks. I held out and finally found ‘San Francisco.’”

Bennett’s two follow-up singles in 1963 charted higher than “San Francisco”: “I Wanna Be Around” hit No. 14 and “The Good Life” peaked at No. 18. His album output perked up, too, with Columbia issuing two new studio albums in ’63 and three in ’64. I Wanna Be Around also reached No. 5 and would be his highest charting album for the next 46 years.

No denying “San Francisco” had changed his life as an entertainer, but it was a comment Sinatra made to Life magazine in 1965 that Bennett said made the difference in how he was viewed professionally.

“For my money,” Sinatra told Life, “Tony Bennett is the best singer in the business, the best exponent of a song. He excites me when I watch him. He’s the singer who gets across what the composer has in mind, and probably a little more.”

Powers at Columbia Records, though, wanted more hits from Bennett and wanted him to add more contemporary material to his repertoire. Other than his ballad rendition of Stevie Wonder’s “For Once in My Life” in 1967, his final Hot 100 hit (No. 91), his albums and singles stopped selling.

“Anyone who sings popular songs and tells you that he doesn’t want a hit song is lying,” Bennett wrote in the liner notes to a 1991 Columbia Legacy box set. “Early in my career, I decided to sing only the best, not realizing that I would run into many men in the business world who would try to get me to sing novelty songs with gimmicks, insisting that the public had the mentality of a 14-year-old.”

Columbia re-signed Bennett in 1968 and then-president Clive Davis continued to have Bennett record pop hits — Beatles songs, “The Look of Love,” “My Cherie Amour” — with no commercial success. At the same time, Bennett was going through a divorce with his first wife, Patricia, and, in 1971, marrying his second wife, Sandra Grant.

Bennett left Columbia — and the U.S. — going to London to host the TV show Tony Bennett From Talk of the Town. Then-manager Derek Boulton secured Bennett a deal with Curb-Polygram, which put him on Verve Records; he made a couple of albums before being dropped.

Despite Columbia offering to re-sign him, Bennett and Bill Hassett, a hotel and real estate magnate from Buffalo, N.Y., joined forces to create Improv Records in 1972, starting with a record by Ruby Braff. Two of Bennett’s two most significant jazz albums came out in that era, The Tony Bennett/Bill Evans Album on Fantasy in 1975 and Together Again on Improv in 1977. While nether charted, Bennett considered the bare bones nature of his collaborations with the pianist Evans vital. “If you can get to a pure simple thing, it always lasts forever,” he said in the liner notes of Concord Music Group’s Complete Improv Recordings set.

The label released about 10 jazz albums and, due to distribution issues, shut down.

Bennett, who performance schedule was largely limited to Las Vegas in the late ‘70s, found himself with money problems, a failing marriage and succumbing to ‘70s drug culture until he overdosed on cocaine in 1979.

“The manager of Lenny Bruce told me he sinned against his talent with his drug habit,” Bennett told Piers Morgan on CNN in 2011 about his decision to stop doing drugs. “That sentence changed my life. I’ve been given this gift. I know how to sing and perform. I’m sinning against this gift and I thought, ‘I am not going to do that any more,’ and I just stopped. I had to, because I thought I was going to lose everything. It wassaid at the right moment, at the right time.”

Bennett reached out to his oldest song Danny who took over as manager, moving his father back to New York, reuniting him with Ralph Sharon, the pianist who left in 1965, and booking him in small theaters and colleges. Bennett returned to Columbia Records, releasing The Art of Excellence in 1986. The first of his 18 albums for the label since returning, it peaked at No. 160, his first Billboard 200 entry in 14 years. He followed it by continuing to return to his roots, recording an album of Irving Berlin songs with jazz musicians such as Dexter Gordon, Dizzy Gillespie and George Benson.

To promote those albums, Bennett started appearing on The Late Show With David Letterman, the late-night talk show that would become crucial in establishing a new audience for him in the 1990s.

In 1989, still discouraged by slumping record sales, Bennett told new management at Columbia Records he was ready to hang it up. New Columbia president Donnie Ienner asked Bennett to come up with a concept that the label could sell. Within days, Bennett came up with Perfectly Frank, a tribute to Sinatra that would hit No. 102 and go on to win the Grammy for Traditional Pop Album.

It led to a second concept album, Steppin’ Out, a tribute to Astaire, and the floodgates opened.

The investments Danny Bennett started making with The Art of Excellence began paying dividends in 1990 when Tony Bennett became the first celebrity written into an episode of The Simpsons. He would then make a Nike commercial, have his music synched in GoodFellas, The Fabulous Baker Boys, JFK and A Bronx Tale and deliver a show-stopping performance of “When Do The Bells Ring For Me” at the 1991 Grammy Awards. To remind audiences of Bennett’s past triumphs, Columbia Legacy issued a four-CD box set, Forty Years: The Artistry of Tony Bennett, that has sold 88,000 copies. (The set was updated in 2004 as Fifty Years).

Perhaps the biggest moment of Bennett’s revival came at the MTV VMAs in September 1993 when Bennett, dressed in a black T-shirt, top hat, sunglasses and a tie, accompanied the Red Hot Chili Peppers’ Anthony Kiedis and Flea – in tuxedos — to present the Video of the Year. Kiedis and Flea joked with Bennett at the podium save for him perfectly singing a snippet of “Give it Away.”

The response was such that Bennett’s video for “Steppin’ Out With My Baby” was then promptly placed in the MTV Buzz Bin, a demarcation of cool in 1993.

MTV continued its association with Bennett, booking him for an Unplugged special in 1994; it would win the Grammy for Album of the Year at the 1995 ceremony. While the strategy was to pair Bennett with lang and Costello, the repertoire was classic Bennett: “Fly me to the Mon,” “They Can’t Take That Away From Me,” “All Of You,” “Old Devil Moon” and other standards.

“I always tried to do good songs,” Bennett told Billboard in 2006. “When the whole rock ‘n’ roll change came in with Elvis Presley, the Beatles and the Rolling Stones, I kept doing good songs. I just kept working. My ambition was never to go to No. 1, over the top bigger than anybody. If I’m sold out (in concert), and people want to come back 11 months later and see me again, I’m successful.”

In 2006, to celebrate his 80th birthday, his Duets: An American Classic featuring performances with Paul McCartney, Elton John, Barbra Streisand, Bono and others became his best-selling album in the Soundscan era, moving 1.95 million copies and peaking at No. 3.

Duets inspired the Rob Marshall-directed television special Tony Bennett: An American Classic, which aired on NBC in November 2006 and would go on to win seven Emmy Awards including Outstanding Variety, Music or Comedy Special and Outstanding Individual Performance in a Variety or Music Program.

When Duets II debuted at No. 1 on the Billboard 200 charts in 2011, Bennett became the only artist at the age of 85 to have a chart-topping album. A documentary tied to Bennett’s 85^th birthday, The Zen Of Bennett, premiered at the Tribeca Film Festival in 2012 .

Bennett received a Grammy Lifetime Achievement Award in 2001, Kennedy Center Honors in 2005 and a year later was named an NEA Jazz Master and received, a Citizen of the World award from the United Nations. The U.N. also commissioned him for two paintings, one for its 50th anniversary. Three of his paintings are part of the Smithsonian Museums’ permanent collections including his portrait of his Duke Ellington that became part of the National Portrait Gallery’s collection in 2009.

Bennett wrote four books: his autobiography The Good Life with Will Friedwald; Life is a Gift, What My Heart Has Seen and Tony Bennett in the Studio: A Life in Art & Music with Robert Sullivan.

Bennett, who marched with Dr. Martin Luther King Jr. in the historic Selma, Ala., march in 1965, raised millions of dollars for the Juvenile Diabetes Foundation and donated his paintings annually for use as American Cancer Society’s annual holiday greeting card.

In 1999, Bennett and his wife Susan Benedetto founded Exploring the Arts to strengthen the role of the arts in public high school education and established the Frank Sinatra School of the Arts in Astoria in 2001.

Though Bennett was rarely seen in the years since his diagnosis, in January the singer congratulated his Love For Sale and Cheek to Cheek collaborator Gaga for her fourth Oscar nomination when the singer was given a nod for best original song for “Hold My Hand” from Top Gun: Maverick. “Congratulations to the amazingly talented @ladygaga on her 4th Oscar nomination!” Bennett tweeted. “Today, Lady Gaga makes history as the first artist to receive three nominations in the Best Original Song category at the #Oscars. So proud of you!”

Besides his wife Susan and son Danny, Bennett is survived by another son, Dae, and daughters Antonia and Joanna, as well as nine grandchildren.