Tony Bennett was one of the giants of American song. Uniquely, he built his career around his devotion to songs from the early 20th century but enjoyed unprecedented success well into the 21st—an age of rapid advancement and contextual collapse. He was a man who, to borrow a phrase from a contemporary he once seemed destined to live in the shadow of, did things his way, seemingly unconcerned how the public would respond—only to surprise us all when we continued to swoon for his musical gifts, decade after decade.
The man born Anthony Dominick Benedetto, whose journey finally came to an end on July 21, 2023 at the age of 96, possessed an intensely trained but spontaneous tenor. His enthusiasm for (and mastery of) the Great American Songbook—that unofficial collection of great jazz, pop and romantic standards—saved a place for long-gone writers and their craft as rock and roll began to dominate the cultural conversation. “To them, it was different,” he told AARP magazine of his repertoire in 2003. “If you’re different, you stand out.”
Here are some songs Bennett would define (or at the very least, transform) in a career that spanned seven decades and redefined not just how long a singing career could last, but how timeless it could all feel.
“Because of You” (1951)
Bennett had been singing in clubs since his teens, and finally had some good luck after a turn in the Army at the end of World War II (an experience that made him a lifelong pacifist). At the turn of the ‘50s, he was signed to Columbia Records as a promising departure from the sound of Frank Sinatra, who would leave the label. His first major single, featuring a dreamy vocal and the orchestral backing of Percy Faith and His Orchestra, would sit at No. 1 on Billboard’s chart for ten weeks straight.
“Rags to Riches” (1953)
Another early Bennett hit that set the template for his career, the chart-topping “Rags to Riches” was a brassy, upbeat number that showcased the singer’s uncanny vocal phrasing. Those dazzling grace notes in the melody and playful experimentation against the rhythm and tempo of the track remained hallmarks of Bennett’s style all through his career.
“Anything Goes,” with The Count Basie Orchestra (1959)
Not long into Bennett’s first decade as a professional musician, Elvis Presley arrived on the scene with a bang. Even Bennett knew that elegant pop would only get him so far—and his live sets had long been marked by an uncanny ability to adjust his voice to imitate the phrasings of some of jazz’s greatest sidemen. Thus, his bold sessions with Count Basie and his orchestra—the first time the ensemble teamed up with a pop singer, and a stunning reminder of how versatile Tony always was.
“(I Left My Heart) in San Francisco” (1962)
Ralph Sharon, Bennett’s longtime pianist and arranger, happened upon this song—written by George Cory and Douglass Cross, and sung in concert by operatic contralto Claramae Turner but never put on record—and gave it to Bennett on a whim when the pair toured the Bay Area in the early ‘60s. Columbia put it on the b-side of “Once Upon a Time” (a song from a new Broadway musical), but radio DJs flipped the single over and made “San Francisco.” Bennett was born in Queens and was a lifelong New Yorker, but this ode to West Coast longing would become his signature tune, winning a Grammy Award for Record of the Year and opening up new opportunities for the singer, including a celebrated appearance at Carnegie Hall.
“Something” (1970)
In 1970, after standards had been all but wiped out by the Beatles, Dylan, the Stones and rest of ’60s rock, Columbia forced Bennet into this stab at merging his jazz-inflect crooning style with the then mainstream musical landscape. Infamously, the singer was so upset by the repertoire that he threw up during recording. Most of material is wildly dated, but Bennett’s distinct style works on this version of a Beatles song. By the time Sinatra got around his cover of “Something” ten years later this George Harrison song was something of a standard, but it was only a few months old when Bennett released it in early 1970.
“My Foolish Heart,” with Bill Evans (1975)
After the failure of Tony Sings the Great Hits of Today!, Bennett parted ways with Columbia and attempted to start his own label. Though Improv Records didn’t sustain itself past a few releases, two of them were stunning, minimalist records that paired the singer with pianist Bill Evans, heard on Miles Davis’ groundbreaking Kind of Blue some 16 years earlier. Their work together is some of Bennett’s most arresting and intimate.
“Steppin’ Out with My Baby” (1993)
Bennett hit bottom after Improv folded in 1977. Most of the earnings from his shows in Las Vegas were going to his cocaine habit and he was having problems with the IRS. He got help from his sons Danny and Dae, struggling musicians with a knack for business. Over the course of a decade, they got their dad sober, cleaned up his tax bill, had him perform in small theaters and colleges, and secured a new deal with Columbia. By the release of 1993’s Steppin’ Out (a tribute to Fred Astaire) Bennett had become an unlikely comeback story. The title track from the stripped-down album got airplay on MTV, and Bennett was a presenter at the 1993 MTV Video Music Awards alongside the Red Hot Chili Peppers.
“They Can’t Take That Away from Me,” with Elvis Costello (1994)
“I’ve been unplugged my entire career,” Bennett quipped when appearing on MTV’s celebrated acoustic series. Backed as always by the Ralph Sharon Trio, the singer made no concessions to a new generation of listeners, but didn’t condescend to them, either; as a result, they’d welcome him with open arms. The special, featuring guest appearances by k.d. lang and Elvis Costello, made waves enough for the accompanying album to take home a Grammy Award for Album of the Year.
“Body and Soul,” with Amy Winehouse (2011)
His legend assured by the turn of the millennium, Tony Bennett entered elder statesman territory in the 2000s, recording star-studded albums of duets. What no one expected was for the projects to chart as well as they did: 2011’s Duets II became the first album by an octogenarian to top the Billboard 200. And it was hardly a victory lap—Bennett championed all of his duet partners, but none as strongly as British soul singer Amy Winehouse, who sadly lost her battle with drug addiction months before the track was released.
“Love for Sale,” with Lady Gaga (2021)
Twenty years after colonizing MTV, Bennett reached the next generation of pop fans—and performers. In 2014, Bennett released an album with Lady Gaga that saw Gaga stepping out from her Mother Monster role to stake a claim as a jazz singer. Cheek to Cheek debuted at No. 1 on the Billboard 200, assuring there would be a follow-up, 2021’s Love for Sale. But this second album was a bittersweet triumph, as Bennett had been waging a private battle with Alzheimer’s since 2016. It’s believed that singing helped keep him as connected as he could be in his final years, with his final public appearance coming in August of 2021, just before the release of Love For Sale. Taped for a final television special, it shows him stunning an audience at Radio City Music Hall as he nails every one of his songs, with Gaga offering poignant support.
