Tony Bennett’s 10 Essential Songs

When Anthony Dominick Benedetto was growing up in Astoria, Queens, during the Depression, his parents couldn’t afford to pay for the singing lessons he wanted. But he had a good teacher close to home: his father, John Benedetto, an immigrant from southern Italy who loved the songs of the old country and sang them to his two sons on their front stoop.

Anthony Benedetto later took the advice of the comedian Bob Hope and adopted the more Americanized stage name Tony Bennett. He enjoyed a long, prolific career until his death on Friday at 96, with plenty of ups and downs, 20 Grammys and an Emmy, in addition to being a Kennedy Center honoree and the first interpretive singer to receive the Gershwin Prize from the Library of Congress.

Voice lessons, however long delayed, were important to his development. After he served in World War II, Bennett studied, thanks to the G.I. Bill, at the American Theater Wing school in Manhattan. When he was still singing in his 90s, he credited his bel canto training — an Italian vocal style that dates back to the 18th century and that emphasizes a light tone — for maintaining his instrument.

Bennett was equally at home with romantic ballads and jazzy saloon songs, and whether he was singing Cole Porter or Stevie Wonder, he brought a huge range, dramatic flair, rhythmic agility and an inquisitive approach to interpreting lyrics. In 1965, Frank Sinatra told Life magazine, “For my money, Tony Bennett is the best singer in the business.” He held on to that distinction for decades to follow.

Here are 10 of his greatest songs.

“The Boulevard of Broken Dreams” (1950)

Bennett had been singing in Bob Hope’s live revue when he was signed to a contract by Mitch Miller, the pop-minded A&R chief at the venerable Columbia Records. In his first single for the label, it’s easy to hear what impressed Miller: Bennett cuts through the Spanish-inflected arrangement of this kitschy 1930s tango with an untethered expression of postwar bravado.

“Strike Up the Band” (1959)

Bennett was a big Count Basie fan, and he especially admired the Basie band’s surging use of dynamics, so he was well prepared for this session. His version of George and Ira Gershwin’s characteristically tricky “Strike Up the Band” lasts just over a minute and a half, but Billy Mitchell’s tenor sax solo is dazzling and it’s hard to name another singer who could navigate the band’s hard, swinging tempo with such élan.

“I’m Thru With Love” (1961)

Like Frank Sinatra before him, Bennett pushed back when Miller tried to steer him toward greater commerciality. Miller was “furious” and stormed out of the recording studio, Bennett later wrote, when the singer insisted on moving away from grand orchestral arrangements to record an album with only a pianist, his sympatico collaborator Ralph Sharon. The jazz standard “I’m Thru With Love” had previously been recorded by Bing Crosby, Sarah Vaughan and Ella Fitzgerald, but Bennett optimized the song’s melancholy tone in this streamlined version.

“The Best Is Yet to Come” (1962)

The album-opening title song from “I Left My Heart in San Francisco” became Bennett’s signature hit, but it’s the jaunty closer that sounds fresher now. He snagged “The Best Is Yet to Come” from a flop Broadway musical called “All American,” and turned it into a standard: Sinatra covered it two years later, and Fitzgerald and Bob Dylan, among others, eventually followed. It remained a concert staple for years, and no song better exemplifies what the critic Mark Rowland once called Bennett’s “radiance of spirit.”

“Don’t Get Around Much Anymore” (1967)

Bennett considered Count Basie and Duke Ellington the two greatest bandleaders he’d ever heard, and with the great Milt Hinton on bass and the Basie regular Joe Newman on trumpet, he swings effortlessly and joyfully on this Ellington jazz standard. Bennett had something close to awe for great jazz musicians, which may be why he never claimed to be part of that tradition. “I’m not a jazz singer,” he often said. “I’m a singer who likes jazz.”

“Something” (1971)

Between 1951 and 1963, Bennett released 19 songs that reached the Top 20 of the Billboard singles chart. Then the Beatles came along and the hits stopped. The Columbia Records honcho Clive Davis pushed Bennett to cover modern pop hits, and on the day he began a new record a new record that included Beatles and Stevie Wonder songs, Bennett vomited, Davis recalled. The singer was a trouper, though; the “woo!” he interjects in the middle of George Harrison’s “Something” is almost convincing.

“Some Other Time” (1975)

Bennett had an affinity for pianists: Art Tatum was an enduring influence, he had a long partnership with Ralph Sharon, and he made one of his best albums with Bill Evans. Though he wasn’t a master of urban ennui on the level of Sinatra, Bennett does wring all the bittersweet rue out of this song, written by Leonard Bernstein, Betty Comden and Adolph Green for the musical “On the Town,” by singing in parallel with Evans’s lyrical, prudent piano.

“I Got Lost in Her Arms” (1986)

For much of the ’70s, the toll of drugs, divorce, tax problems and depression wore Bennett down. Then his son Danny took over as his manager and engineered a return to Columbia Records. Maybe more significantly, Bennett reunited with Sharon and recorded his acclaimed comeback with just piano, bass, drums and an orchestra. His voice was now rougher, but especially on his version of Irving Berlin’s “I Got Lost in Her Arms,” he adjusted by infusing his lower register with savvy understatement.

“When Do the Bells Ring for Me” (1990)

Bennett loved the Great American Songbook, but eventually, a prolific singer runs out of pre-rock standards and needs to find slightly younger material. So Bennett was delighted when, in a restaurant one night, he heard the piano bar stalwart Charles DeForest perform a song he’d written, “When Do the Bells Ring for Me” It became a concert showcase for Bennett, thanks to its climactic high notes, and when he sang it at the Grammys in 1991, he got a standing ovation.

“I Get a Kick Out of You” (2021)

Biographically, Bennett couldn’t have had less in common with Cole Porter, a Midwesterner born to substantial privilege. But Porter’s giddy use of double and triple rhymes was perfect for Bennett’s rubato trickery, so his second album with Lady Gaga was a Porter-only affair, released five years after Bennett was given a diagnosis of Alzheimer’s disease. And let’s be honest, it’s a kick to hear a 95-year-old master sing, “Some, they may go for cocaine.”