I remember when Tony Bennett died just a couple years ago in July of 2023, less than two weeks shy of his 97th birthday. It wasn’t just the end of one singer’s rich and diverse seventy-year career as a steward of The Great American Songbook. It was the end of an era. It’s an overused phrase, I grant you, but on the occasion of Bennett’s passing, it was fitting.
Although his recording career technically didn’t begin until 1950, he was the last of the generation of entertainers who flourished during World War II and the years immediately after. He was a good twenty-five years behind Bing Crosby, who was performing professionally as early as 1923. Frank Sinatra, Dean Martin, Nat King Cole and Ella Fitzgerald all launched their careers in a narrow window between 1934 and 1935. Even Rosemary Clooney’s career pre-dated Bennett’s by a couple years.
Nevertheless, Tony Bennett and his music are deeply rooted in the same period as all of these others—squarely in the middle of the 20th century, a time when the right voice paired with the right song was a recipe for timeless magic. And perhaps even more so than the others, he found a way to navigate the dramatic changes on the landscape of American popular music throughout the latter half of the century and beyond and remain relevant until the very last performances of his career in 2021. In the end, he appealed not just to fans from his own generation, but also to those who were decades younger.
Even Sinatra, one of the most iconic singers and entertainers of the 20th century, didn’t hesitate to publicly acknowledge the magnitude of Bennett’s talent. His comment in a 1965 Life magazine interview said it all:
“For my money, Tony Bennett is the best singer in the business…He’s the singer who gets across what the composer has in mind, and probably a little more.”
I always thought Sinatra’s assessment of Bennett spoke volumes about both men.
Bennett was born Anthony Dominick Benedetto 100 years ago this month, on August 3, 1926. By the age of ten, he was engaging in two artistic pursuits, singing and drawing. He studied painting and music at the School of Industrial Art in New York City but dropped out at age 16 to help support his family. He took several low-skilled, low paying jobs to earn money, but also worked as a singing waiter and performed at various amateur nights around the city.
His musical aspirations were interrupted when he was drafted into the U.S. Army to serve during the last months of World War II, but he came home in 1946 and got right back to singing. He shortened his name to Bennett and signed to Columbia Records in 1950. His early hits included “Because of You,” “Cold, Cold Heart” (previously made famous by Hank Williams), “Rags To Riches,” and the Kismet show tune, “Stranger in Paradise.”
Throughout the late 1950s and early ‘60s, Bennett added layers of texture and nuance to his voice by incorporating elements of jazz into his style. It turned out to be a strategy that served him well for the remainder of his career. Several of his recording projects during this period were collaborations with jazz artists like Art Blakey, Nat Adderley and Count Basie.
In 1962, he recorded a little-known song called “I Left My Heart in San Francisco.” The track earned Grammy Awards for Record of the Year and Best Male Solo Vocal Performance. It eventually became his signature song.
But his career had stalled by the late ‘60s due to the industry’s hard shift toward rock music. Like many singers of his generation, Bennett made a few attempts to record covers of contemporary rock and pop songs, but the results were generally unsuccessful. His 1970 release, Tony Bennett Sings the Great Hits of Today!, took a beating from the critics.
By the late ‘70s, he was doing very little performing outside of the Vegas circuit, which led to financial struggles. In addition, he had developed a drug addiction that nearly killed him in 1979.
With the help of his son Danny working as his manager, Bennett turned it all around in the 1980s. He kicked the drug habit, and the father-son partnership found a way to introduce the singer to younger audiences who were discovering the music of their parents’ generation. By the age of sixty, Bennett had re-signed to Columbia Records and begun the process of self-reinvention that led to the most critically and financially successful phase of his career.
There were strategic appearances on late night TV and even MTV programming. There were innovative and ambitious recordings that celebrated The Great American Songbook, but with an eye toward younger audiences. He didn’t hesitate to perform alongside artists like k.d. lang and Elvis Costello, but he never sacrificed his commitment to his musical roots and sensibilities.
“Tony Bennett has not just bridged the generation gap, he has demolished it,” The New York Times said in 1994. “He has solidly connected with a younger crowd weaned on rock. And there have been no compromises.”
He was awarded the Grammy Lifetime Achievement Award in 2001 (one of eighteen Grammys he won between 1993 and 2021), and he received a Kennedy Center Honor in 2005.
His 2006 album, Duets: An American Cassic featured collaborations with a who’s who of rock and pop artists representing a range of styles, including James Taylor, Paul McCartney, The Dixie Chicks, Sting, Bono and Diana Krall. The recording won a Grammy for Best Traditional Pop Vocal Album. A 2011 followup album, Duets II, revisited the concept and featured performances with Norah Jones, Willie Nelson, Amy Winehouse, John Mayer, Queen Latifah, Lady Gaga and others.
While Bennett’s musical career was flourishing in the 1990s and 2000s, the world was also discovering his artwork at the same time. His paintings and drawings—which he signed as Anthony Benedetto or just Benedetto—were featured in two art books: Tony Bennett: What My Heart Has Seen in 1996, and Tony Bennett in the Studio: A Life of Art & Music in 2007. The latter was a bestseller. His Boy on Sailboat, Sydney Bay is in the permanent collection at the National Arts Club on Gramercy Park in New York City, as is his Central Park at the Smithsonian American Art Museum in Washington, DC.
“It would take me a lifetime to learn to explain myself as an artist,” he once said. “As you grow older, you learn what to do and what to leave out. You kind of simplify your work and get the same thing done with fewer strokes.”
He may have been talking about painting, but the comment is an indication of how well he understood the creative process in general.
Despite an Alzheimer’s diagnosis in 2016, Bennett continued to perform and record until the COVID-19 pandemic in early 2020. His connection to reality became increasingly tenuous over time, but his continued commitment to singing reportedly helped him stay focused. His final live performances were two shows at Radio City Music Hall with Lady Gaga in early August of 2021, right around his 95th birthday.
Somewhere during the later decades of his career, he suggested that his success as an entertainer and his happiness as a person were a matter of mindest as much as anything else. “I’m not the type of person who likes to look backwards,” he said. “I’ve always felt compelled to move forward and I’ve never been one to dwell in the past. All the people I’ve met, all the places I’ve been, and all the things that I’ve done have simply been part of who I am.”
Musical trends come and go. Tastes and opinions change, sometimes in a matter of months. In the end, the meaning of words like “good,” “better” and “best” is completely subjective. But Tony Bennett proved over the course of seventy years that any art—musical, visual or otherwise—made from a place of honesty, dedication and hard work will ultimately endure.
Sinatra may have been right about him all along.