Tony Bennett in Billboard’s Back Pages: From ‘Bobby-Sox Crowd’ Favorite to Elder Statesman

When Tony Bennett died July 21 in his hometown of New York at the age of 96, the world lost one of the last great interpreters of the American Songbook. Billboard has 32 years on Tony — although we can only wish we had such unflagging class and charisma — and we have to admit that we greeted the crooner with a “Cold, Cold Heart” when he debuted in 1951. But we quickly came to appreciate the way he flew us to the moon.

‘Cry’-ing Shame

When 24-year-old Anthony Dominick Benedetto rebranded himself as Tony Bennett and debuted on Columbia Records, Billboard didn’t exactly bet on the “Rags to Riches” singer. The May 12, 1951, issue called “I Won’t Cry Anymore” a “competent etching” and dismissed “Because of You” as an “adequate” song “with nothing special to offer.” By the time the latter track topped Billboard’s pre-Hot 100 pop chart, Bennett’s performances routinely “bowled over the bobby-sox crowd,” according to the Sept. 29, 1951, issue. Hey, we’re a trade publication — not Nostradamus.

Golden Gate, Golden Pipes

Over the next decade, as Bennett delivered a series of era-defining hits, Billboard was full steam ahead on the Tony train. “Ol’ pro Tony leaves ’em gasping,” raved a Dec. 8, 1962, review of a Carnegie Hall concert. “Tony, like a crafty veteran pitcher in baseball, grew stronger as the night grew longer.”

Saving Face

An in-depth interview in the Nov. 30, 1968, issue found the crooner getting candid: “The trend in the music business was moving away from me,” he said. “I held out and finally I found [‘I Left My Heart in San Francisco’] and had my first hit record after a long dry spell.” Bennett also said he had stuck to his guns when Hollywood called, revealing that one studio floated a “contract that called for remodeling his nose.” His reply? “I liked my nose then, and I like it today.” His praises were also sung by a chorus of all-star supporters, including Duke Ellington, Bob Hope and even jazz pioneer Louis Armstrong. “If Tony Bennett who swing sings wonderfully can’t send you,” Armstrong said, “there’s a psychiatrist right up the street from you. DIG him.”

Plugged In to the Next Generation

“Bennett continues his reign as the crooning choice of Generation X,” reported the July 2, 1994, Billboard in the wake of his hit MTV Unplugged album, asking, “What will Grandma do to rebel? Start buying White Zombie CDs?” Bennett’s cross-generational appeal didn’t wane over the next two decades. “Tony Bennett achieves his first No. 1 album on the Billboard 200 with Duets II, making the 85-year-old the oldest living artist to reach No. 1,” reported the Oct. 8, 2011, issue. Three years later, Bennett beat his own record when he returned to No. 1 on the Oct. 11, 2014, chart at age 88 with Cheek to Cheek, his album with Lady Gaga. The record still stands.

The Good Life

“I feel on top of the world,” Bennett told Billboard in an Aug. 11, 2016, interview. “I’m singing well. The audience loves what I’m doing. All I can tell you is I have a blessed life.”

This article originally appeared in the Aug. 26, 2023 issue of Billboard.