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Tony Bennett, one of the most beloved and recognizable vocalists in the history of American pop music, died Friday at 96, less than two weeks shy of his birthday.

Bennett’s professional career spanned eight decades and achieved a No. 1 album at age 85. He was diagnosed with Alzheimer’s disease in 2016, but continued to perform and record through 2021.

Born Anthony Dominick Benedetto in Queens, New York, on August 3, 1926, to Italian Immigrant parents, he began singing as a child and studied music and painting at New York’s High School of Industrial Art.

Bennett served in the US Army in World War II and was part of the 255th Regiment that liberated the Kaufering concentration camp in Landsberg, Germany, which was 30 miles south of the Dachau concentration camp.

Bennett’s career as a recording artist began in 1949 and he was one of the biggest singers in the ’50s and early ’60s. Some of his most popular songs included I Got Rhythm, The Best is Yet to Come, The Shadow of Your Smile and I Left My Heart in San Francisco, the latter of which won him his first Grammys. Decades later, he famously dueted with Amy Winehouse, released a full-length duet album with Diana Krall, recorded with Lady Gaga and did duets with Mariah Carey.

He is survived by his wife Susan Benedetto, his two sons, Danny and Dae Bennett, his daughters Johanna Bennett and Antonia Bennett, and nine grandchildren.