Tony Bennett (1926–2023), legendary crooner

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By Linnea Crowther July 21, 2023

Tony Bennett was an iconic singer who brought traditional pop standards to generations of listeners in a singing career that spanned eight decades.

Bennett’s enduring legacy

In later years, Bennett became known for his devotion to the traditional tunes that first made him famous in the 1950s, as well as for his determination to avoid retirement. He stayed relevant and beloved long after the retirements and deaths of many of his peers, introducing his favorite songs to Gen-Xers and millennials. He may have been an anachronism, but he made the music of the past work in a way that surprised even the contemporary audiences that loved it. Yet before he was the elder statesman of standards that he became in the 1990s and beyond, Bennett was a teen idol.

Early life

Born Anthony Dominick Benedetto Aug. 3, 1926, Bennett grew up in Depression-era New York City and went to work to help his family after his Italian immigrant father died when Tony was just 10. He learned the value of hard work from his seamstress mother, gaining a work ethic he’d carry with him for the rest of his life.

“One of the early gifts I got was from my mother,” he told NBC’s “Today” show in 2007. “She always insisted on top quality. She would make those penny dresses, and the more she made, the more money she would earn. But even still, she’d throw away a bad dress. Always quality. Ever since, I never wanted to do a song that would insult the audience. That’s the way to make music that lasts. Like a dress that lasts.”

Young Bennett dropped out of school at 16, working as a copy boy for The Associated Press in support of his family. But music was in his genes. He remembered being told about his father’s history in his Italian hometown: “The legend in my family was that he used to stand at the top of a mountain, and the whole valley would hear him sing.” Inspired by his father’s love for music as well as his own burgeoning talent, Bennett took a job as a singing waiter.

War years and a career on the rise

Bennett began performing around the city and gaining a reputation as a skilled amateur, but World War II interrupted the beginnings of his career. Having turned 18 in 1944, Bennett was drafted into the U.S. Army in the final year of the war and served on the front lines in Europe. Bennett’s experience of the horrors of war helped turn him into the peace-loving civil rights activist he would become.

“I’m anti-war,” he told Howard Stern. “It’s the lowest form of human behavior.”

Bennett returned home after helping liberate a Nazi concentration camp and playing in an Army band in the year after the war’s end. He threw himself back into his musical career, studying and performing every chance he got. His first big break came courtesy of Pearl Bailey (1918–1990), who had heard him play and asked him to open for her at a performance attended by Bob Hope (1903–2003). Hope, too, liked what he heard. He invited the young singer on a short 1949 tour with him and graced him with his stage name – because, Hope said, Anthony Benedetto was just too long for a marquee.


Major success was soon to follow Bennett’s lucky break. He inked a record deal with Columbia Records, signed by legendary producer Mitch Miller (1911–2010). Bennett became a star in 1951, riding high on the charts with songs including “Because of You” and “Blue Velvet.” Fans loved his smooth crooner’s tones, and the same young women who screamed in the front row of his concerts lined up by the hundreds in black mourning clothes when he married Patricia Beech in 1952.

Bennett may have been taken, but his tunes still stirred the hearts of listeners. Further hits followed, including “Rags to Riches” (1953), “Chicago” (1958) and “I Left My Heart in San Francisco” (1962), the song that would become Bennett’s signature. By 1964, he sounded as smooth as ever, but listeners were attracted to a new sound, one very different from the syrupy-sweet standards Bennett crooned. The British invasion was in full swing, and the Beatles and their peers were dethroning the crooners from the tops of the charts.

A dark period

Bennett’s music wasn’t exempt from the change in tastes, and his career began to flounder. Bennett was urged to modernize his sound with a recording of rock songs. He complied reluctantly, though he didn’t like the music and wasn’t sure how to interpret it. The album was both poorly received by the public and repellent to Bennett himself. He later remembered in a biography, “I actually regurgitated when I made that awful album – I got physically sick.” Rock ‘n’ roll wasn’t the answer for Bennett, but wide audiences were no longer interested in the classics that Bennett interpreted so well. He spiraled downward throughout the 1970s, fighting drug addiction and the IRS.

Revitalized career

It was his son, Danny Bennett, who helped turn things around for Bennett. Danny took over as his father’s manager and helped get his finances under control. He envisioned a new direction for his father’s career, one that built upon the solid foundation of Bennett’s work from the 1950s and ’60s. Danny urged his father out of the nightclubs and dives and into small venues frequented by young people. The key to Danny’s plan was that Bennett would not change his style by revisiting his disastrous rock recordings of the ’70s. Instead, he would present his young audiences with the songs he’d always sung, the standards of the Great American Songbook, many of which would be entirely new to the listeners whose parents were children when Bennett’s career was young.

The new approach worked. After early forays into marketing his music toward the young and hip, Bennett recorded an “MTV Unplugged” concert in 1994, appeared on “The Simpsons,” and teamed with alternative-rock radio stations to play benefit concerts. All the while, he was singing the standards that were his bread and butter, and the young audiences were listening.

“To them, it was different,” he told AARP, The Magazine. “If you’re different, you stand out.”

Bennett’s fortunes reversed, and his near bankruptcy was a thing of the past. He flourished under the renewed attention, collaborating with contemporary artists including Amy Winehouse (1983–2011), Queen Latifah, and Carrie Underwood. He was back on the charts, his 2014 record with Lady Gaga, “Cheek to Cheek,” debuting with a Billboard No. 1. Bennett, at 88, was the oldest artist ever to make such a stellar debut. The pair won a Grammy Award for their effort and embarked on a tour together, sharing the spotlight as co-headliners. He released a second album with Lady Gaga in 2021, “Love for Sale,” his final release.

A different kind of crooner

What made Bennett unique as a singer stemmed from a piece of advice he took from an early music teacher, who told him not to imitate other popular singers such as Frank Sinatra (1915–1998). Instead, he was urged to take inspiration from the instruments that make up a jazz band. Bennett listened to the piano music of Art Tatum and the saxophone solos of Stan Getz (1927–1991), and he modeled his vocal phrasing on what he heard. It helped him created a sound all his own, one that would never be mistaken for Sinatra or any other singer.

Bennett was also renowned for his big voice and his ability to belt out a song all the way to the back of the theater. Even in his later years, he typically took a moment during a concert to set aside the microphone and sing one tune – often “Fly Me to the Moon” – with simply the strength of his own voice. Audiences never had to strain to hear him.

Painting career

As illustrious and long-lived as Bennett’s musical career was, it almost took a back seat to another of the star’s talents: visual art. He was an artist from a young age, one who loved to draw and thought he might pursue a career as a commercial artist. Music won, but Bennett never forgot his love for art, painting throughout his life and exhibiting his work around the country at venues including the Smithsonian American Art Museum and the Butler Institute of American Art. He explained to The Wall Street Journal that his two favorite art forms went hand in hand: “I’ve found that the creative choices made when painting are similar to judgments made when singing. Both are about line, form, and color – and both have different levels of depth.”

Bennett frequently donated his art – both musical and visual – to benefit the causes that were important to him. Proceeds of a painting’s sale might support a foundation while many benefit concerts included a performance by Bennett. He co-founded Exploring the Arts, a nonprofit organization that works to provide quality arts education in schools. A devoted civil rights supporter, he participated in the 1965 Selma to Montgomery marches in Alabama. He also denounced apartheid, refusing to perform in South Africa while the system of racial segregation was in place.

Awards and honors

In addition to winning 18 Grammy Award statues and a separate Grammy for lifetime achievement, Bennett was honored with tributes including the National Endowment for the Arts Jazz Masters Award, the Kennedy Center Honors, and a star on the Hollywood Walk of Fame. His commitment to social justice was noted with the United Nations High Commissioner for Refugees Humanitarian Award and induction into the International Civil Rights Walk of Fame.

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