Remembering Tony Bennett, The Painter

Tony Bennett was a music legend and pop-culture icon, but casual fans might not realize that he was also an accomplished painter. In between selling 50 million records and winning 20 Grammys, the late singer also devoted his time to visual arts, working mainly with watercolor and oil paint.

“I found, even as a kid, I’d draw or paint away and all of a sudden it was my own little creation,” Bennett explained in the 2007 book Tony Bennett in the Studio: A Life of Art & Music. “I was shocked by it, in a way. I’d say, ‘Look at that. Look at that thing I made.’”

Bennett began drawing at age 5, making his mark with sidewalk chalk outside his home in Queens. In his teen years, he studied both music and art at the High School of Art and Design (then called the School of Industrial Arts). At the time, he preferred art class, because as he told WQXR in 1981, he found “music classes [to be] terribly boring.”

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His priorities soon shifted, but as Bennett’s singing career took off, his love for painting never diminished—and neither did his desire to learn as much as he could about art. “I’ve studied a lot. I’m studying right now. I’m studying portrait painting right now. I’ve had nothing but good teachers,” Bennett said during a 1988 interview with Spin magazine. “I like to go to schools, like the Academy of Art down in the Village. That’s a fantastic place. You have to learn form before you can be free, and they teach the old Michelangelo techniques of studying the bones and then the muscles and then the skin and then the shadings. You learn from the bottom up. And I like that kind of traditional teaching. There are no shortcuts, and if you do it the right way, it really gets good. I love the whole process.”

After Bennett’s death at age 96 on July 21, 2023, tributes poured in praising his talent as a musician, but still others nodded to his love of art. “Today we mourn the passing of legendary New York singer, Tony Bennett,” read a tweet from Central Park’s official account. “Tony was an incredible friend to the Park, where he loved painting wildlife and foliage scenes later in his life.”

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Bennett did indeed love to paint landscapes, both of his New York City hometown and the places he saw during his decades of world travel, but he was an accomplished portraitist as well. His 1993 painting of fellow music icon Duke Ellington is part of the Smithsonian’s collection at the National Portrait Gallery. The work was unveiled at the museum in 2009 to commemorate the 110th anniversary of Ellington’s birth.

While the Ellington portrait is probably Bennett’s most famous painting, it was actually the third artwork he donated to the Smithsonian. In 2002, he donated a portrait of Ella Fitzgerald to the National Museum of American History, and in 2006, the Smithsonian American Art Museum received one of his paintings of Central Park.

According to Bennett, Ellington was the person who encouraged him to take his art more seriously in later years after his music career became his main focus. “He told me it was better to be creative in more than one field and he was so right,” Bennett told Long Island Weekly in 2015. “I love the fact that when I am not performing I can stay in a creative zone and paint, and then when I am done painting, it’s time to hit the stage again and perform.”

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Bennett signed all of his work with his given name, Anthony Benedetto, so it’s certainly possible that you could see one of his paintings and not know that the singularly talented crooner was responsible for it. Plenty of other famous people did know, however, and celebrities including Oprah Winfrey, Katie Couric and former President Bill Clinton all have original Benedettos in their collections.

In 2016, Bennett was diagnosed with Alzheimer’s disease, but he continued making art for as long as he could. The Art Students League of New York exhibited a collection of his later work as recently as 2019. That show included an ink sketch of Lady Gaga, who famously collaborated with Bennett on two duet albums, Cheek to Cheek and Love for Sale.

Bennett’s own favorite artists included Michelangelo, John Singer Sargent and David Hockney. In the case of Hockney, the affection was mutual. “LeRoy Neiman and David Hockney and Elaine de Kooning, these are the top people in the art world and they’re saying I know how to paint,” Bennett told Spin. “I say, ‘Oh, you’re just saying that to make me feel good,’ and they say, ‘Oh, no, you’re a painter, a strong painter. Just keep painting.’ And it’s very encouraging. It lifts me up. It gets me inspired.”

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