Tony Bennett: How Many No. 1 Hits Has the Legendary Singer Had?

It’s rare for a singer to have the adoration of music fans, the esteem of critics, and the respect of fellow musicians. To have all that and be successful for decades is unheard of. Then there’s Tony Bennett (1926-), who’s had and done all that for eight decades and counting.

In Forty Years: The Artistry of Tony Bennett, the four-disc set that took stock of his career (to that point) in 1991, Bennett’s admirers filled the pages of the accompanying booklet. “For my money, Tony Bennett is the best singer in the business — the best exponent of a song,” Frank Sinatra said.

Louis Armstrong, Bing Crosby, Duke Ellington, Judy Garland, and so many others have echoed those words over the years. And Bennett’s work with Lady Gaga in the 2010s brought renewed fame and recognition from yet another generation. Bennett’s earned every bit of it, and his success in the recording industry dates back to the early ’50s.

Tony Bennett has notched 3 No. 1 singles in his career

Harold Arlen and Tony Bennett work at the piano in the '50s
American composer Harold Arlen (1905-86) and American singer Tony Bennett rehearse in the late 1950s. | Authenticated News/Getty Images

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It might sound like a joke to say that Bennett was landing No. 1 hits before there was a Billboard Hot 100, but that’s actually the case. If you check Bennett’s page on the Billboard site, you’ll find him with zero chart-topping singles.

Billboard’s Hot 100 (aka “the pop charts”) didn’t go into effect until the late ’50s. By then, Bennett had already gone to No. 1 on three separate occasions. Bennett first got on top with “Because of You,” his ’51 stunner that commanded the No. 1 slot for 10 weeks.

Bennett followed that with “Cold, Cold Heart,” his recording of the Hank Williams original that was the first time a country record featured strings. After landing on the charts in July, it spent six weeks at No. 1. Bennett had brought country to the top of America’s pop charts.

Bennett wasn’t done yet. His ’53 recording of “Rags to Riches” spent a whopping eight weeks at No. 1. Fans of Goodfellas will know that rendition well: Martin Scorsese dropped it into the movie early on. But “I Left My Heart in San Francisco,” perhaps Bennett’s signature song, didn’t crack the top 10. (It peaked at No. 19.)

Bennett has 2 No. 1 albums, 1 of which he recorded with Lady Gaga

Duke Ellington holding a knife to cut a cake while Tony Bennett smiles next to him
Composer Duke Ellington and singer Tony Bennett cut the cake at a party in circa 1965. | Michael Ochs Archives/Getty Images

In the era of the long-playing (LP) record, Bennett had his first top-10 hit with I Left My Heart in San Francisco, the ’62 album featuring his timeless rendition of the title track. That went to No. 5, as did I Wanna Be Around (1963), another signature Bennett recording.

Bennett kept recording through the end of the 20th century (and into the 21st). In 2006, his Duets album shot to No. 3 on the Billboard charts; Bennett was back. Five years later, he came back with an even bigger hit record featuring Lady Gaga, Amy Winehouse, and Aretha Franklin (among others).

Duets II shot to the top of the charts, giving Bennett his first No. 1 album in his 80s. After a No. 5 duets album with Latin recording artists, Bennett tasted No. 1 again with Gaga. Their Cheek to Cheek (2014) was another smash hit.

It’s fitting that Bennett’s biggest hit albums were collaborations. It’s hard to think of a more generous and caring man in the industry. Duke Ellington might have said it best. “He’s a big, beautiful man,” Ellington is quoted saying in Forty Years. ‘He’s totally unselfish in a way completely unique in the theater.”