Tony Bennett, whose huskily expressive voice and warm, welcoming manner made him one of the foremost popular singers of the last eight decades, died Friday at his home in Manhattan. He was 96.
His publicist, Sylvia Weiner, announced his death.
Mr. Bennett had revealed in 2021 that he had Alzheimer’s disease.
The winner of 19 Grammy Awards, one of them for lifetime achievement, Mr. Bennett was the last great interpreter of the classic American popular song. He belonged to a line that began with Bing Crosby in the 1920s, reached its zenith with Frank Sinatra in the ’50s, and, in the person of Mr. Bennett, maintained an exceedingly high standard down to the present. How high? Crosby called Mr. Bennett “the greatest singer I ever heard.” Sinatra considered him “the best singer in the business, the best exponent of a song.”
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Unlike Crosby and Sinatra, Mr. Bennett found himself embraced by the rock generation. His appearance at the MTV Music Awards in 1993 drew widespread attention and led to a “Tony Bennett Unplugged” concert on MTV. The resulting CD was the largest popular success of his career. “I Left My Heart in San Francisco” may have been Mr. Bennett’s signature tune, but “Unplugged” was its signature event. It was a recognition of his special ability to bridge generations, eras, styles.
Mr. Bennett sold some 50 million records over the course of his career. In 2011, his “Duets II’’ album went to the top of the Billboard charts. At 85, he became the oldest recording artist to have a number one record. Three years later, he broke that record again, with an album of duets with one of his singing partners from that earlier release, Lady Gaga. The two released a follow-up, Mr. Bennett’s final recording, in 2021. Their pairing was further evidence, not that any was needed, of the universality of his appeal. Long since a classic himself, Mr. Bennett had no difficulty extending his classicism to others.
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Along with Sinatra, Mr. Bennett belonged to the bel canto tradition of such Italian male pop vocalists as Russ Columbo, Vic Damone, Al Martino, Buddy Greco, Dean Martin, and Perry Como.
Yet Mr. Bennett’s popularity owed nothing to the Mediterranean good looks and Latin-lover image customarily associated with such singers. His sleepy eyes, scimitar nose, and pronounced chin made his face a caricaturist’s dream. That very homeliness underscored the sense of sincerity and lack of affectation he projected.
Mr. Bennett was never comfortable with show-biz flash. He was “incapable of sounding slick,” the critic Will Friedwald writes in his book “Jazz Singing.”
“There’s a quality about it that lets you in,” the composer Alec Wilder once said of Mr. Bennett’s voice. Calling him “a consummate entertainer,” the jazz critic Francis Davis added that Mr. Bennett “also happens to be the decent sort of fellow you’d be happy to find on the next barstool.” Sinatra, whom Mr. Bennett called “my favorite singer,” put it best. “You can only be yourself,” he told him in 1957. “But you’re good at that.”
Mr. Bennett was good at many things. Even as his large, dark-toned voice allowed him to envelop a song, the seeming effortlessness of his phrasing meant there was never any risk he’d overpower a lyric. His taste was superior. “I’ve always tried to do the cream of the popular repertoire and yet remain commercial,” he said in a New Yorker magazine interview. He utilized very effectively a bravura dynamic range, something he learned to do from his friend Judy Garland.
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As most notably demonstrated in his several recordings with Count Basie, Mr. Bennett had a very sure rhythmic sense and could swing a song with a jazzman’s ease. The National Endowment for the Arts named Mr. Bennett one of its Jazz Masters in 2005. He cited the virtuoso jazz pianist Art Tatum as his most important instrumental influence and the Swing Era singer Mildred Bailey as his most important vocal influence.
Mr. Bennett’s talents extended beyond singing. A gifted painter, he had his first gallery exhibit in 1971, in London, and first museum retrospective in 1994 at the Butler Institute of American Art, in Youngstown, Ohio. Three of his works are in the collection of the Smithsonian Institution.
The sense of sincerity and dedication that Mr. Bennett brought to his artistry extended to the social realm. As a soldier in Germany, he ate with a Black friend, a violation of the Army’s segregation policy that earned him a demotion and assignment to a graves-registration unit. Twenty years later, he joined Martin Luther King Jr. on the 1965 Alabama march from Selma to Montgomery. “I am as proud (more proud, really, in many ways) to have been a small part . . . of his march,” Mr. Bennett wrote in his 2016 book, “Just Getting Started,” “as I am of any Grammy Award or gold record.”
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Anthony Dominick Benedetto was born on Aug. 3, 1926, in Queens, N.Y., the son of John Benedetto and Anna (Suraci) Benedetto. He was the first member of his family to be born in a hospital. Mr. Bennett’s father, the owner of a small grocery store, died when his son was 10. His mother went to work as a seamstress to support him and his older brother and sister. Mr. Bennett dropped out of high school and started singing in amateur shows under the name Joe Bari.
Drafted in 1944, he served in the Army and saw action in France and Germany during the closing months of World War II. An officer who heard him singing in the shower had Mr. Bennett transferred to special services, where he began performing for his fellow troops.
After leaving the Army, Mr. Bennett used the GI Bill to study singing at the American Theatre Wing in New York. He worked as a singing waiter and appeared on “Arthur Godfrey’s Talent Scouts” program, where he lost to Rosemary Clooney. The singer Pearl Bailey gave him a spot in her nightclub revue. When Bob Hope saw the act, he asked Mr. Bennett to appear with him. It was Hope who suggested Tony Bennett as a stage name.
Mr. Bennett signed with Columbia Records in 1950, an association that would last 21 years, then resume again with Mr. Bennett’s comeback in the ’80s. He would record more than 80 albums for the label.
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Mr. Bennett’s first Columbia release was “The Boulevard of Broken Dreams.” The next year he had his first No. 1 hit, “Because of You.” It was followed by a string of gold records: Hank Williams’s “Cold, Cold Heart,” “Rags to Riches,” “Stranger in Paradise,” and “In the Middle of an Island.”
As the ‘50s drew to a close, Mr. Bennett’s music began to evolve. The arrival of rock underscored the essential mediocrity of the material Mr. Bennett was being saddled with by Mitch Miller, Columbia’s head of artists and repertoire. His work began to assume a more jazz-oriented feel with such LPs as “Cloud 7,” “The Beat of My Heart,” and the Basie recordings.
In 1962, Mr. Bennett enjoyed a dual triumph. He made his Carnegie Hall debut and released “I Left My Heart in San Francisco.” Originally the B side to a song called “Once Upon a Time,” it earned Mr. Bennett his first two Grammys and another gold record. He donated the latter to the City of San Francisco. The song became Mr. Bennett’s trademark, and he claimed never to tire of singing it.
It took several years for the growing dominance of rock to take a toll on Mr. Bennett’s career. He released what would remain a personal favorite among his recordings, “The Movie Song Album,” in 1966. Among its tracks was the theme song from his film debut, “The Oscar” (1966). Playing an agent with the improbable name of Hymie Kelly, Mr. Bennett earned such poor notices that the film role was his last as well as first. The recipient of two Emmy Awards, Mr. Bennett fared better on the small screen.
After being dropped by Columbia, Mr. Bennett started his own label, Improv. He recorded several albums, most memorably two superlative sessions with the jazz pianist Bill Evans in the mid-’70s. He then went nine years without a new release.
Mr. Bennett’s son Danny, a former rock musician, became his manager in 1979. He got his father back on Columbia and oversaw a series of well-received concept albums — including tributes to Irving Berlin, Sinatra, and Fred Astaire — which helped pave the way for his MTV appearances. Even at the height of his early success, in the ‘50s, Mr. Bennett had never been hip. Now he was. “Tony Bennett Unplugged” won a Grammy for album of the year. He appeared in ads for Nike and was an early guest voice on “The Simpsons.” He appeared as himself on such TV series as “30 Rock” and “Entourage” and showed up as “Phony” Bennett on “Saturday Night Live.” Mr. Bennett’s cameo vocal at the end of “Analyze This” (1999) got the hit comedy one of its biggest laughs.
In 2005, Mr. Bennett was a Kennedy Center honoree.
His marriages to Patricia Beech and Sandra Grant ended in divorce. In addition to his son, Danny, he leaves his wife Susan; daughters Johanna and Antonia; another son, Dae; and nine grandchildren.
Asked once to account for his success, Mr. Bennett replied, “The trick, really, is to learn all the rules and then throw it all away and be yourself.”
Mark Feeney can be reached at mark.feeney@globe.com.