Tony Bennett was one of the giants of American song. Uniquely, he built his career around his dedication to early 20th century songs, but he enjoyed unprecedented success well into the 21st – an era of rapid progress and contextual breakdown. He was a man who, to use a phrase of a contemporary whom he once seemed destined to live in the shadows of, did things his way, seemingly indifferent to how the public would react – only to surprise us all when we continued to swoon for his musical gifts, decade after decade.
Born Anthony Dominick Benedetto, whose journey finally came to an end on July 21, 2023 at the age of 96, possessed an intensely trained yet 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 came to dominate the cultural conversation. “It was different for them,” he said AARP magazine of his repertoire in 2003. “When you’re different, you stand out.”
Here are some songs that would define (or at least transform) Bennett in a career that spanned seven decades and redefined not only how long a singing career could last, but how timeless it all could feel.
“By you” (1951)
Bennett had been singing in clubs since he was a teenager and finally got some luck after taking a job in the army at the end of World War II (an experience that turned him into a lifelong pacifist). In the early 1950s, 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 voice and the orchestral accompaniment of Percy Faith and His Orchestra, would chart at No. 1 on Billboard‘s chart for ten consecutive weeks.
“From poor to rich” (1953)
Another early Bennett hit that was the foundation of his career, the chart-topping song “Rags to Riches” was a brassy, upbeat track that showcased the singer’s eerie vocal phrasing. Those dazzling notes of grace in the melody and playful experimentation against the song’s rhythm and tempo remained a hallmark of Bennett’s style throughout his career.
Anything goes, with The Count Basie Orchestra (1959)
Not long after Bennett’s first decade as a professional musician, Elvis Presley burst onto the scene with a bang. Even Bennett knew that elegant pop would only take him so far – and his live sets have long been characterized by an uncanny ability to modify his voice to imitate the phrasing of some of jazz’s greatest sidemen. Such are daring sessions with Count Basie and his orchestra – the ensemble’s first time collaborating 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, chanced upon this song – written by George Cory and Douglas 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 and made “San Francisco.” Born in Queens, Bennett was a lifelong New Yorker, but this ode to the longing for the West Coast 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 performance at Carnegie Hall.
In 1970, after standards had all but been wiped out by the Beatles, Dylan, the Stones and the rest of ’60s rock, Columbia pushed Bennet into this attempt to fuse his jazzy crooning together. style with the then mainstream music landscape. The singer was notorious for being so upset by the repertoire that he vomited during the recording. Most of the material is massively dated, but Bennett’s signature style is well suited to this version of a Beatles song. By the time Sinatra got around to his cover of “Something” a decade later, this George Harrison song was something of a standard number, 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 big hits of today!, Bennett parted ways with Columbia and attempted to start his own label. While Improv Records didn’t hold up after a few releases, two of them were stunning, minimalist records that paired the singer with pianist Bill Evans, featured on Miles Davis’ groundbreaking Sort of blue some 16 years earlier. Their work together is one of Bennett’s most compelling and intimate.
“Steppin’ with My Baby” (1993)
Bennett hit rock bottom after Improv folded in 1977. Most of the revenue from his Las Vegas shows went towards his cocaine addiction and he had problems with the IRS. He received help from his sons Danny and Dae, struggling musicians with a knack for their business. Over the course of a decade, they sobered up their father, cleaned up his tax bill, got him to perform in small theaters and colleges, and struck a new deal with Columbia. By the release of 1993’s Stepping out (a tribute to Fred Astaire) Bennett had become an unlikely comeback story. The stripped-down album’s title track aired 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 From Me,” with Elvis Costello (1994)
“I’ve been unplugged my whole career,” Bennett joked when he appeared on MTV’s celebrated acoustic series. Supported as always by the Ralph Sharon Trio, the singer made no concessions to a new generation of listeners, but he also did not condescend to them; as a result, they would welcome him with open arms. The special, which featured guest appearances from kd lang and Elvis Costello, made enough of a stir for the accompanying album to take home a Grammy Award for Album of the Year.
“Body and Soul”, with Amy Winehouse (2011)
His legend secured through the turn of the millennium, Tony Bennett entered elder statesman territory in the 2000s, recording star-studded duet albums. What no one expected was that the projects would be as well mapped as they were: those of 2011 Duets II became the first album by an octogenarian to top the chart Billboard 200. And it was hardly a victory lap – Bennett defended 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’s release.
“Love for Sale”, with Lady Gaga (2021)
Twenty years after colonizing MTV, Bennett reached the next generation of pop fans – and artists. In 2014, Bennett released an album with Lady Gaga in which Gaga stepped out of her Mother Monster role to file a claim as a jazz singer. Cheek to Cheek debuted at number 1 on the Billboard 200, to ensure there would be a sequel, 2021’s Love for sale. But this second album was a bittersweet triumph as Bennett had been battling Alzheimer’s since 2016. It is believed that singing helped him stay as connected as possible in his final years, with his last public appearance coming in August 2021, just before the release of Love for sale. Recorded for a final television specialit shows him wowing an audience at Radio City Music Hall as he nails all of his songs, with Gaga providing poignant support.