Tony Bennett, the masterful vocalist widely beloved for his interpretations of the Great American Songbook, has died. He was 96.

Multiple news outlets report that Bennett died in his hometown of New York. His publicist did not give a cause, but Bennett had been diagnosed with Alzheimer’s disease in 2016.

Bennett had a career that lasted eight decades, during which he sold more than 50 million records worldwide, won 19 Grammy Awards, the Grammy Lifetime Achievement Award, and two Primetime Emmy Awards. He was named an NEA Jazz Master and a Kennedy Center Honoree.

Moving effortlessly between pop and jazz, Bennett was a champion of the Great American Songbook known for his captivating takes on the classic music of the Gershwins, Cole Porter, Irving Berlin, and many more. Among the songs he was best-known for singing were “The Way You Look Tonight,” “Body and Soul,” and his signature song, “I Left My Heart in San Francisco.”

Bennett was known to collaborate with a variety of other artists, including Lady Gaga, Amy Winehouse, Aretha Franklin, Frank Sinatra, k.d. lang, and Diana Krall.

Bennett was widely respected by his peers. In 1965, Sinatra called him “the best singer in the business. He excites me when I watch him. He moves me. He’s the singer who gets across what the composer has in mind, and probably a little more.”

Born Anthony Dominick Benedetto on Aug. 3, 1926, Bennett began singing at an early age. After fighting in the final stages of the Second World War, he returned home and developed his singing technique, signed with Columbia Records, and notched his first No. 1 pop hit “Because of You” in 1951.

As he continued to refine his artistry throughout the 1950s, Bennett began to show a taste for jazz. In 1957, Ralph Sharon became Bennett’s pianist, arranger, and musical director, and he encouraged Bennett to lean even further into jazz. That year, he released The Beat of My Heart, a popular and critically acclaimed album that featured well-known jazz musicians such as Herbie Mann, Nat Adderley, Art Blakey, and Jo Jones. He then went on to work with the Count Basie Orchestra, becoming the first male pop vocalist to sing with Basie’s band. Together, they recorded the albums Basie Swings, Bennett Sings (1958) and In Person! (1959). Meanwhile, Bennett was also making a concerted effort to bolster the reputation of his nightclub act, taking the example of Sinatra and other top singers of jazz and standards at the time.

In 1962, Bennett released his recording of “I Left My Heart in San Francisco,” which was then a little-known song originally written for an opera singer a decade prior. Both the single and the album of the same title achieved gold status, and the song won two Grammy Awards, including record over the year. Over the years, it became known as Bennett’s signature song.

As rock ‘n’ roll became the dominant musical force of the late ’60s and ’70s, Bennett insisted on sticking with the classic pop of the Great American Songbook. He struggled greatly during that time; his popularity waned, and he bounced between record labels, developed a drug addiction, and ran into tax problems. After a near-fatal cocaine overdose in 1979, Bennett called his sons Danny and Dae for help. “Look, I’m lost here,” he told them. “It seems like people don’t want to hear the music I make.” Danny signed on as his father’s manager, got his expenses under control, moved him back to New York, and began booking him gigs while seeking to give him a new image. By 1986, Tony Bennett had re-signed to Columbia Records and released The Art of Excellence, charting for the first time in nearly 15 years.

In the ’90s, Bennett continued to perform and seek favour with a younger audience, despite making no changes to his appearance, singing style, musical accompaniment or song choices. The plan worked, as Bennett gained new fans with appearances on Late Night with Conan O’Brien, The Simpsons, Muppets Tonight, and several MTV programs. In 1994, The New York Times wrote: “Tony Bennett has not just bridged the generation gap, he has demolished it. He has solidly connected with a younger crowd weaned on rock. And there have been no compromises.” That year, his album MTV Unplugged: Tony Bennett went platinum and won the coveted Grammy Award for album of the year.

Bennett continued to record and perform into his nineties. In February of 2021, it was revealed that Bennett had been living with Alzheimer’s disease for the past five years. Still, he recorded music with Lady Gaga during that time and released their second duo album Love for Sale in 2021 — which won to Grammys and was nominated for album of the year — and he gave his final performances before retiring in August.

Bennett leaves his wife Susan, daughters Johanna and Antonia, sons Danny and Dae, and nine grandchildren.