Tony Bennett at Home: Inside the Legendary Crooner’s Colorful Home Life

Jazz legend Tony Bennett—whose 100th birthday would have been August 3—managed to play a role in a handful of the most significant moments of the last century. During World War II, he fought in the Battle of the Bulge. He helped liberate a concentration camp, he marched with Martin Luther King Jr. during the Civil Rights Movement, and he performed for no fewer than 11 US presidents.While the singer won two Grammy Awards for “I Left My Heart in San Francisco,” he spent most of his life in New York. Born Anthony Dominick Benedetto to Italian immigrants in Astoria, Queens, he was given his stage name by none other than Bob Hope, who saw the young vet performing in Greenwich Village in 1949 and said, “Come on, kid, you’re going to come to the Paramount and sing with me,” before adding, “We’ll call you Tony Bennett.” At the time of his death at age 96, Bennett was living in a penthouse overlooking Central Park. In the years between, he cultivated a life defined by art, political activism, and giving back to the city he loved. (Bennett and his third wife, Susan Benedetto, were instrumental in founding the Frank Sinatra Jr. High School of the Performing Arts in his birthplace of Astoria.)The 10 photos below show Bennett in the places he called home, each filled with records and art supplies. And given how often the term appeared in his catalog, with tracks called “That’s My Home,” “Home Is the Place,” and “I’ve Come Home Again,” no doubt he left his heart in every single one.Bennett at home with family in 1955 Photo: David McLane/NY Daily News Archive via Getty ImagesA Bronx taleBennett was already a world-famous nightclub performer in 1951 when he looked out into the audience at Moe’s Main Street in Cleveland and spotted Patricia Ann Beech on a date. “I could see her from the stage—she was sitting ringside—and I was taken with her beauty,” the crooner wrote in his autobiography, The Good Life. He proposed onstage at the Paramount in New York, and the pair were married at St. Patrick’s Cathedral in 1952, as thousands of young girls surrounded the Manhattan church dressed in black to mourn the marriage. (Bennett alleged that the outpouring of grief may have been organized by his manager.) By the time this photo was taken in 1955, the couple, shown here with their older son D’Andrea “Danny”, were living in Briar Oaks, a luxury apartment building in the Riverdale neighborhood of the Bronx.Tony Bennett in his New Jersey residence in 1957 Photo: David McLane/NY Daily News Archive via Getty ImagesJersey boysAfter the 1955 birth of the Bennetts’ second son, Daegal “Dae”, “Patricia and I decided it was time to get a house in the suburbs where the kids could spread out,” Bennett wrote in The Good Life. In 1957, they purchased a home on Lydecker Street in Englewood, New Jersey, where the pair is shown in this photo from the same year. Here, Bennett is working from home, recording a song.Bennett loved painting still life, landscapes, and cityscapes. Photo: Graphic House/Archive Photos/Getty ImagesNatural talentIn this 1960 snap, Bennett is shown with a rake in the garden of his New Jersey home. Though he wasn’t known for his gardening, Bennett’s appreciation for nature was evident in one of the other art forms he had a talent for: painting, which he did under the name Tony Benedetto. He usually worked outdoors and was often quoted saying, “I always paint nature. Nature is the boss.”Bennett bought a home for his mother after experiencing early success as an entertainer. Photo: Bettmann/Contributor/Getty ImagesLifelong learnerBennett, who continued painting throughout his life, is shown here in 1963 working on a landscape piece at home in Englewood. He attended New York’s School of Industrial Art before dropping out at age 16 to work and help support his widowed mother. He was drafted at 18 and, after the war, pursued singing at the American Theatre Wing—an education funded by the GI Bill. Bennett’s success as a singer allowed him to buy his mother a place near his own. “I became a performer to stop her from working. I succeeded in getting her a house in New Jersey,” Bennett once said of his mom. There were definitely perks to having her nearby. “Duke Ellington and I were close friends—so close that his entire band once came over to my mother's house in New Jersey for an Italian dinner,” Bennett told the Wall Street Journal in 2013.Bennett and family pictured in 1963 Photo: Bettmann/Getty ImagesFamily timeIn the living room of their Englewood home, the Bennett family listens to records while cuddling with their cats. While the image looks idyllic, the family’s residence there (from 1957 to 1971) was not always harmonious. Bennett’s touring complicated the relationship; he and Patricia split in 1965, two years after this photo was taken. They finalized the divorce in 1971. “The Christmas season of 1965 was the worst I’d lived through since the time I was 10 and my father died,” Bennett wrote of that time in his book Just Getting Started. “I wasn’t welcome at our family home in New Jersey, and I missed my two sons. I was living in a small, spiritless room in the Gotham Hotel and felt sad, depressed, and lonely, yet too embarrassed to admit that to anybody and ask for companionship or cheer. For me, the season was cold and gray.”Bennett pictured with his wife, actor Sandra Grant, and their two daughters Photo: Richard Corkery/NY Daily News Archive via Getty ImagesHollywood yearsBennett met actor Sandra Grant in 1965 on the set of his film The Oscar. They married in 1971. The couple moved to Los Angeles together and are shown here in 1977, at home with their daughters Joanna and Antonia (who was suffering from the sniffles). Bennett’s Hollywood years were difficult ones; the record label Bennett launched had failed, and he ran into issues with the IRS on back taxes. He also struggled with substance abuse, which led to a near-death experience when IRS pressures grew: “A golden life enveloped me in a warm glow. It was quite peaceful…. But suddenly, I was jolted out of the vision.” His wife found him in the tub, revived the singer, and rushed him to the hospital. “The only thought on my mind was something my ex-manager Jack Rollins had told me about Lenny Bruce right after Lenny’s death from an overdose. All Jack said was, ‘The man sinned against his talent.’ That hit home. I realized I was throwing it all away, and I became determined to clean up my act.”Bennett painting a still life in 1983 Photo: Audrey C. Tiernan/Newsday RM via Getty ImagesThe artist at workBennett and Grant split up in 1979, and by the time this 1983 photo was taken, the singer had moved back to New York. There, he reunited with two of his true loves: Central Park, where he went to paint landscapes, and the Metropolitan Museum of New York, which he frequented to admire the work of artists he admired—his favorite being John Singer Sargent. “I keep learning how to paint,” Bennett told The New York Times in 2015. “I try to learn how the masters do it.”Tony Bennett had four children. Photo: Eddie Sanderson/Getty ImagesA proud fatherAfter Bennett moved back east, he hired his son Danny as his business manager. Danny booked him on late-night talk shows and for TV appearances on everything from Sesame Street to MTV, which opened the door for younger generations to discover his talents. He went on to collaborate with artists including Amy Winehouse and Billy Joel, even touring with Lady Gaga in 2014 at the age of 88. Here, Bennett is pictured in 2002 enjoying the company of his son Danny and daughter Antonia in his Manhattan aerie.Bennett pictured with his dog, Boo. Photo: Eddie Sanderson/Getty ImagesMan’s best friendBennett poses with his Maltese, Boo, in this 2002 portrait. His other faithful companion at the time was Susan Crow Benedetto, whom he met backstage after a concert when she was the 19-year-old president of his fan club. After a 20-year courtship, the pair married in 2007. “She brought balance and contentment into my life,” Bennett wrote about Susan in Just Getting Started. “Her goodness and the peace at the center of her soul have helped me to think straight, live well, and, I’m quite sure, live longer. His prediction turned out to be true; Susan was Bennett’s caregiver after he was diagnosed with Alzheimer’s in 2016, up until his death in 2023.New York was Bennett’s favorite city. Photo: Eddie Sanderson/Getty ImagesA walk in the parkFrom his move back to New York in the early ’80s to his death in 2023, Bennett lived in a series of apartments chosen for their views of Central Park. He estimated that he had painted over 800 landscapes of the green space. “The more I paint, the more I realize just how beautiful life around me is,” Bennett wrote in Life is a Gift: The Zen of Bennett. “I live in New York City, in a place overlooking Central Park, and I love it here because there’s nature right outside my window. I get to see the four seasons change every year, which is magnificent. The city is always vibrant and so alive. Everywhere you turn, there is so much that inspires me. In New York, I never run out of subjects to paint. This is my favorite place to live, over any other city on earth.”