The legendary crooner Tony Bennett, a giant in the history of American popular music, has died. According to the Associated Press, Bennett’s publicist Sylvia Weiner confirmed that he passed away this morning in his New York hometown. No specific cause of death has been reported, but Bennett was diagnosed with Alzheimer’s disease in 2016. Bennett was 96, and he was two weeks away from turning 97.

Anthony Dominick Benedetto was born in Queens in 1926. His father, an Italian immigrant, worked as a grocer, while his mother, a first-generation Italian-American, was a seamstress. Bennett’s father died when he was 10. By that time, he was already singing. At 10, Bennett performed alongside mayor Fiorello La Guardia at the opening of the Triborough Bridge. As a teenager, he worked a number of jobs, sometimes making money as a singing waiter at Italian restaurants in Queens. Bennett also studied commercial art in high school, but he dropped out at 16.

Bennett was drafted into the Army at the end of World War II, and he fought in the Allied invasion of France and Germany, helping to liberate the Landsberg concentration camp. After the war, Bennett remained stationed in Europe, where he adapted the stage name Joe Bari, which he only kept for a little while, and sang with army bands. When he got his discharge, Bennett used the GI Bill to study music, and he learned the bel canto singing style that Frank Sinatra had popularized. In 1950, Bob Hope discovered Bennett when he opened for Pearl Bailey at a Greenwich Village nightclub. Bennett became Hope’s opening act, and in 1950, Mitch Miller signed Bennett to Columbia.

Mitch Miller produced Tony Bennett’s 1951 debut single “Because Of You,” which became a #1 hit and sold more than a million records. Later that year, Bennett landed a second #1 hit with a jazz-infused cover of Hank Williams’ “Cold, Cold Heart.” In Bennett’s early career, Mitch Miller produced all of his singles, while Percy Faith arranged the orchestra. Bennett’s sound became jazzier and brassier in the next few years, as he returned to #1 with 1953’s “Rags To Riches.” As a singer, Bennett radiated warmth and generosity, and his conversational sense of timing made him immediately recognizable.

During the ’50s, Tony Bennett sang a number of Broadway standards, and he hosted a short-lived TV variety show. He recorded with jazz musicians like Herbie Mann, Art Blakey, and Nat Adderley, and he made two full-length albums with the Count Basie Orchestra. In 1962, Bennett followed Judy Garland as the second pop singer to perform at Carnegie Hall. Bennett’s 1962 version of “I Left My Heart In San Francisco” was only a modest hit upon release, but it won a Grammy for Record Of The Year became Bennett’s signature song over the years. In 1965, Frank Sinatra said that Bennett was “the best singer in the business.”

Tony Bennett was always a relatively old-fashioned singer, and his style of singing became less and less central to pop in the ’60s. At the behest of Clive Davis, he tried covering the Beatles and singing more up-to-date material; the experiment was not successful. But Bennett kept recording, and he also became a and advocate for civil rights and other left-wing causes. He marched with Martin Luther King, Jr., and he lated campaigned against things like apartheid and the Iraq War.

Bennett left Columbia for Verve and later formed his own short-lived label Improv. He almost died of a cocaine overdose in 1979. At that point, Bennett owed the IRS a ton of money, but his son Danny took over as his manager and eventually stabilized his career. In 1986, Bennett sang “Life In A Looking Glass,” the theme song for the Blake Edwards film That’s Life!, and it was nominated for an Oscar.

In the early ’90s, a series of appearances on late-night TV led Tony Bennett to become a semi-ironic favorite among alternative rock audiences. Two of his albums in that period, 1992’s Perfectly Frank and 1993’s Steppin’ Out, went gold. In 1993, he put on a Dr. Seuss top hat to present alongside the Red Hot Chili Peppers at the VMAs. On a 1994 episode of MTV Unplugged, Bennett sang his classics, and he duetted with Elvis Costello and k.d. lang. The resulting LP became the surprise winner of a Grammy for Album Of The Year. In 1995, when I was 15, I saw Bennett put in a surprise appearance at the HFStival, an alt-rock radio-station festival in Washington. Bennett performed in between Soul Asylum and the Ramones. I can say that I moshed and smoked a blunt as Tony Bennett performed.

Tony Bennett kept touring and performing well into his nineties, and his voice remained remarkably undiminished. He duetted with Amy Winehouse on a 2011 version of the standard “Body And Soul.” It was the last thing that Winehouse recorded before her death, and it made Bennett the oldest artist ever to chart on the Billboard Hot 100. In 2014, Tony Bennett and Lady Gaga released Cheek To Cheek, their first album of duets. Bennett and Gaga also toured together, made a TV special, and appeared in a Barnes & Noble commercial.

Bennett retired from performing in 2021, and he and Lady Gaga released another album, Love For Sale. It was Bennett’s final album. Love For Sale made the top 10 of Billboard‘s album charts, and it earned Bennett another Album Of The Year nomination at last year’s Grammys. Shortly after its release, Gaga joined Bennett to perform a pair of farewell concerts at Radio City Music Hall.

Below, watch some videos of Tony Bennett at work.