Tony Bennett’s Voice Made People Smile for Half a Century

Everyone loved Tony Bennett for the same reason he loved Louis Armstrong: “The minute you heard him, just the first two bars, everyone started smiling. He made everybody smile."

There was a contagious joy in his voice, and a kind of enviable contentment, things they don’t teach in music school. He had all the things they do teach too, the phrasing and pitch and timing, but he never flaunted those skills. Listening to him sing, you might not think, what a great artist. But what you were likely to think, and what the singer wanted you to think, was, what a great song.

Tony Bennett’s voice made people smile for a very long time. Long enough, in fact, to get him into the Guinness Book of World Records just for longevity alone: “longest time between the release of an original recording and a re-recording of the same single by the same artist.” Almost 69 years passed before he revisited George and Ira Gershwin’s 1924 standard “Fascinating Rhythm.” Bennett originally recorded the song in 1949 and again in 2018 with Diana Krall. That wasn't his only time at the Guinness rodeo. In 2014, he and Lady Gaga recorded Cheek to Cheek, an album released when Bennett was 88 years old, making him the oldest person to ever top the U.S. charts (he also set the record for the longest lapse between top 20 albums in the U.K).

Tony Bennett Duets with Amy Winehouse, John Mayer, Lady Gaga, & More

Bennett, who died on Friday at 96, had his first hit record, “Because of You,” in 1951, and sold more than a million copies. That same year, his recording of Hank Williams’ “Cold, Cold Heart” also topped the charts.

He won the first two of his 20 Grammys in 1963, for “I Left My Heart in San Francisco,” which became his signature song. It won Best Solo Vocal and Record of the Year.

Thirty years passed before Bennett won another Grammy in 1993, but after that, the floodgates opened. Between 1993 and 2018, he won 17 more, many of them for duet collaborations with singers whose parents were children when he first started making records, including Bono, John Legend, Diana Krall, George Michael, Queen Latifa, Amy Winehouse, Aretha Franklin, Willie Nelson, Natalie Cole, and Lady Gaga, with whom he recorded an entire album of standards, and who was to share the stage with him at his farewell concert at Radio City Music Hall in 2021.

A true musical patriot, Bennett delved deep into America’s melting pot of song. “I’m from New York City,” he explained in a 1983 interview. “In New York City, the schooling you get is usually from a Black teacher or a Jewish teacher, and in my life, I’ve gotten to love the teachers I had. I’ve had some wonderful teachers, very bright and very with it. I’m an Italian, of Italian descent, and I sing Black and Jewish music. This is what I do—I’m very influenced by the jazz artists. But, I love the music of Gershwin, Harold Arlen, and Irving Berlin, Arthur Schwartz.”

The composers of the 1930s were a continuous wellspring for his interpretations in a career that spanned over seventy years. “I’m in love with the music that they wrote, but they contributed to the United States. They are the greatest ambassadors of the United States for the United States. I go to places as far off as Japan, Manila, Australia. No matter where I go in the world—France, any foreign country—if I sing ‘Dancing in the Dark’ by Arthur Schwartz, everybody knows that song. They know Cole Porter’s ‘Night and Day.’” To him, “These are not old songs, they’re great songs, and I also think of them as America’s folk songs. I think that they are true folk songs. And what a level of folk music. What a high level of popular music! As long as we’re existing on this planet, our songs will become more and more amplified.”

There is no mystery around what kind of singer Tony Bennett was. Time and again, he called himself an interpreter. “I like to cut straight on interpretation,” he said in a 1982 interview. He didn’t buy into the pressure or critical requirement to be a singer/songwriter. “To me, there’s a great minimization of interpreters, but to me interpreters make songs live—Judy Garland, Frank Sinatra, Nat King Cole—they interpreted,” he explained. “Today, we’re kind of bent on the fact that popular musicians should also compose their own songs. That’s very ambitious, but there’s only a few Charlie Chaplins around, and there’s only a few Cole Porters around. And, I’d hate to match my talent against theirs when it comes to the craftsmanship of writing the songs. So, I put my energy on interpreting the music—American music—and trying to do what the composer has in mind.”

Anthony Dominick Benedetto was born in New York City on Aug. 3, 1926, to John Benedetto Sr., a grocer, who emigrated from Reggio Calabria, Italy, and Anna Suraci Benedetto, an American-born Italian seamstress. Tony shared a flat above his father’s grocery store with his parents and an older brother and sister—John Jr. and Mary. Shortly before their father became ill and succumbed to heart disease, John Sr. was forced to sell his grocery store, and the Benedetto family fell into poverty. Bennett was nine years old when his father died at the age of 41. The children moved to Astoria Queens with their mother, who continued mending dresses, charging a penny per dress.

“It was different,” he said of his childhood after his father’s death during the Great Depression. “It was sad not to have a father, and very confusing. But, it’s funny. It just shows you, when people love one another, how many things really work out.”

Music always filled the Benedetto home. Before emigrating, Tony’s father had sung arias from the mountaintops for all the valley villagers to hear when he still lived “in Podàrgoni, a little town out in Calabria, Italy.” In America, the family spun opera records—Gigli and Caruso, Richard Tucker (young Tony was also listening hard to Bing Crosby)—and Tony’s brother John Jr. was, according to Tony, “a magnificent prodigy, you know. He was a very wonderful opera singer. They called him ‘The Little Caruso.’ He was 13 and sang solo spots in the Metropolitan Opera and did radio shows in those days.” To hold his own, Tony became the family comedian, imitating Al Jolson and Eddie Cantor. At family gatherings, he was the showstopper, and his early talent was obvious enough that just after his father’s death, he was invited to sing at the opening of the Triboro Bridge, where he received a pat on the head from Mayor Fiorello LaGuardia. At 15, Bennett left high school to work as a singing waiter to help support his family.

Big crescendos and holding some of the higher notes as he sang made Tony Bennett more interesting than most contemporary vocalists singing traditional pop. He practiced bel canto technique to keep his voice rich and pure to the point of never really modifying songs to suit his aging voice. It remained bright. But, perhaps his early exposure to opera had something to do with it as well.

Two years later, in 1944, he was drafted, which he described in his autobiography, The Good Life. Asked to choose between the Army or Navy, he chose the Navy, “and the guy stamped, ‘Army.’ I thought, ‘Oh, boy, so that’s the way it’s going to be.’” He was assigned to the 63rd Infantry Division and arrived in Europe shortly after the Battle of the Bulge. Within days, half the replacement troops he’d shipped out with were injured or killed.

“A front row seat to hell,” is how Bennett described his march through France and Germany as a front-line soldier. He watched his comrades die, and dug fox holes in the frozen ground so he and his fellow soldiers could sleep—their proximity to Germans was often close enough for them to hear their conversations. The thrum of anxiety was ever present and heightened by detonating explosives. As the war concluded in April 1945, and concentration camps were being liberated, Bennett was assigned to the camp at Kaufering in Landsberg, Germany. After seeing things “no human should have to see,” he had a brief moment of happiness. That May, Bennett was showering when a passing officer heard him singing. Bennett was persuaded to join the 255th regiment band, which led to a kinder, gentler assignment -- Special Services, which served as diversionary entertainment away from the amorous temptations of German women.

The atrocities of war did little to mend divisions along racial lines. Rampant racism compounded an already hellish experience. Back in boot camp, it was bad for an Italian kid under the authority of an “old-fashioned Southern bigot” drill sergeant, and, as Bennett recalled, “it was just as bad for other ethnic groups, especially the Blacks and Jews.” It did not get better. On Thanksgiving 1945, having shared a meal with a Black soldier, Corporal Bennett was ceremoniously demoted by a ranking officer who, in a big show of assholery, sheared Bennett’s stripes with a razor from his uniform and spat on them. “It was actually more acceptable to fraternize with the German troops,” Mr. Bennett mused, “than it was to be friendly with a fellow Black American soldier.” (It was these injustices—along with a long history of collaboration with artists like Duke Ellington and Count Basie—that inspired Bennett’s participation in the 1965 Martin Luther King march for Civil Rights in Alabama.)

Now relegated to Private, Bennett was tasked with exhuming bodies of fallen soldiers from mass graves until his good fortune was again restored. Appalled by the demotion, a major helped get him off grave duty and into The 314th Army Special Services Band, where he became Joe Bari, the band’s singer.

Joe Bari returned from war as a committed pacifist. “Fighting is the lowest form of human behavior,” he wrote. “It’s amazing to me that with all the great teachers of literature and art, and all the contributions that have been made on this very precious planet, we still haven’t evolved a more humane approach to the way we work out our conflicts.”

By 1949, Joe Bari was discovered by Bob Hope while singing with Pearl Bailey in her Greenwich Village revue. Hope invited Bari to perform with him at the Paramount Theatre, and took him on tour—but not before christening him Tony Bennett.

In 1950, Bennett signed with Columbia Records, and had a few hits under his belt, “Because of You” and “Just in Time,” and he had a nice run with Count Basie, a pairing he credits to the oft-criticized record producer Mitch Miller—the same Mitch Miller who conceived the first country-to-pop crossover when he had Tony cover Hank Williams’ “Cold, Cold Heart.”

“I Left My Heart in San Francisco,” Bennett’s signature song, was released in 1962. His first two Grammy Awards—Best Solo Performance and Record of the Year—were awarded for the album by the same name. A string of Tony Bennett hits followed. Almost all of them have histories that preceded Tony Bennett’s stamp, stories he shares in interviews and between songs.

“I Want to Be Around,” his 1963 hit, was co-written by Johnny Mercer and Sadie Vimmerstedt, an Ohio beautician and amateur songwriter who sent a letter to Mercer with the idea and the first line—"I want to be around to pick up the pieces when somebody breaks your heart," a lyric she wrote after Frank Sinatra left his first wife for Ava Gardner. Bennett received letters from Vimmerstedt written from around the world until her death in 1986.

There were dark times when audiences weren’t given much from Bennett. With rock acts like the Beatles, the Rolling Stones, and Bob Dylan dominating the charts, young hearts weren’t throbbing to jazz standards. Clive Davis, then president of Columbia Records, pressured Bennett to modernize and cover ’60s pop songs. “It’s hard to cover Janis Joplin,” he laughed. “It really did get that silly, OK? It got that stupid.”

The result was Tony Sings the Great Hits of Today! The cover art is an ill-conceived, groovy caricature of Bennett lounging in bell bottoms wearing a psychedelic necktie. It was laughable, and he knew it. Of all the “Tony Sings…” albums, it’s the only one that uses an exclamation point in the title in anticipation of its own failure. Much as his mother disliked working on cheap dresses, Tony Bennett didn’t like performing “inferior material.” The recording industry lost interest in traditional pop artists, so, after twenty-three years, Tony Bennett left CBS/Columbia Records. “I just had to say, look I’m going to take a break, because I was there twenty-three years, and I always kept the company in the black, you know.” From Bennett's perspective, he didn’t need to modernize. He was releasing three standards a year that the public bought—just one would help the entire company.

Bennett found only limited fulfillment and industry representation in London, where he lived for three years, but his efforts were largely ignored. So, he returned to the U.S., started his own record label, Improv, and recorded two LPs worth of Rodgers and Hart songs, Tony Sings 10 Rodgers & Hart Songs and Tony Sings… More Great Rodgers & Hart. While the Improv label didn’t have the wide distribution that Columbia afforded, the 1970s was a prolific period. He wasn’t chasing the numbers in the charts the way pop music does. He was creating classics, and performing with musicians on his list of greats, like Bill Evans. The Tony Bennett/Bill Evans Album was such a joy to record, and, as Bennett explained, “so well received by the connoisseurs of the music business that we decided to do a second album. Lucky that we did, because now we have two full albums.” Together Again was recorded in 1977. “It’s something I cherish very much. I just love it. I just love the fact that I sang with Bill Evans.” he said.

In time, the stinkers by great performers become masterpieces in their own right. Tony Sings the Great Hits of Today! holds up to scrutiny, because the songwriters were blue-ribbon. Burt Bacharach, Jimmy Webb, John Lennon, Paul McCartney, George Harrison, Stevie Wonder among names less recognizable. The album was included in the Barnes & Noble exclusive, Tony Bennett: The Complete Collection.

Somewhere in the '70s, things began to unravel for Bennett. Vegas by then was passe and pretty gross. And while it still had stages and lounges, and while Tony Bennett could always fill seats, it was Fat Elvis or Liberace or Wayne Newton who topped the marquee. Bennett was just one more crooner.

By the close of the decade, Bennett had a failing second marriage, a $2 million tax debt, no professional representation, and a raging cocaine addiction. “Cocaine flowed as freely as champagne,” he recalled, “and soon I began joining the festivities. At first it seemed like the hip thing to do, but as time went on, it got harder and harder to refuse it when it was offered.”

After a nearly fatal overdose, Bennett woke up to the pile of garbage he had created in all his excess. His son, Danny, from his first marriage, didn’t have a college degree. He did have blue hair and had his heart set on a career in a punk band. Fortunately, Danny also had a head for crisis management, business, and public relations. First, he tackled the IRS debt and saved his father’s home. Then, he reinvigorated Tony Bennett’s career by marketing him as a “living American legend.” By the mid-eighties, Bennett was back with Columbia doing what he’d always done—singing standards. Two years later, Bennett was charming the 18-24-year-old record-buying demographic by appearing on Late Night with David Letterman to sing a segment theme for “Supermarket Finds.” And, he still had the loyalty of older fans. By the late nineties, Danny had done so well at getting his dad’s finances in order that Tony could have retired over twenty years ago.

He credited Danny with the inspiration to meld vintage Bennett and his old standards with modern voices, the likes of which astounded him. “Queen Latifa is as good as Ella Fitzgerald,” he said of her voice on their recording of “Who Can I Turn To?” He compared Amy Winehouse to Dinah Washington, a compliment that helped calm her when the immensity of performing with Tony Bennett on “Body and Soul” got to her. “Next to Judy Garland,” Bennett said, “k.d. Lang was the best singer” he ever heard.

Drawing and painting were his other passions. “God is Love” Duke Ellington has a place in the National Portrait Gallery collection at the Smithsonian, and Central Park is one of the Luce Foundation Center’s 20th Century Paintings. Central Park inspires the feeling of sitting in a top-floor apartment overlooking one of New York City’s most iconic landmarks and massive green space. It speaks to the artist’s versatility and undeniable talent, but it also feels like a work created by a native New Yorker. Anyone familiar with the city can easily place themselves beneath the autumn foliage in Central Park and imagine wandering inside it. Bennett estimated he painted about 800 Central Park vignettes.

Perhaps the secret to the longevity that Tony Bennett has enjoyed is perception, something Frank Sinatra, at another backstage-at-the-Paramount Theater encounter, taught him. By the time he met Sinatra, however, he had two million-selling records, “Because of You” and “Cold Cold Heart.” “I felt nervous about an audience,” Bennett remembers, and he taught me that the audience are your friends. They come to see you. And he changed my whole psychology: there’s no such thing as a bad audience. There’s a bad performance, but there’s not a bad audience.”

Over the course of his career, many contributed to his stagecraft. One night, during a particularly low point in Bennett’s career, pianist Bill Evans, who accompanied him on the 1977 album Together Again, called and dropped an unsolicited pearl of wisdom. "Just go with truth and beauty tonight,” Evans said. “Leave it at that."

But it’s his own instinct that leaves his audiences craving more. “Know when to get off. You can’t stay out there too long. You have to be aware when you've done enough.” Tony Bennett never overstayed his welcome.

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