Tony Bennett Popular Song Rankings [2025]
He is an Italian-American and is hailed in the United States as a top male vocalist and entertainer.
Despite his advanced age, he shows no signs of slowing down and continues to perform energetically.
Here is a collection of many of his popular songs.
Tony Bennett Popular Song Ranking [2025] (1–10)
SmileTony Bennett1rank/position

It has been used in commercials such as Suntory “BOSS Silky Black,” Kirin Free, and SoftBank’s “iPhone 5.” The song originally appeared in Charlie Chaplin’s film Modern Times and had no lyrics at the time.
In the 1950s, English lyrics were added, and artists like Nat King Cole sang it, leading to a renewed appreciation of the song.
Cheek To CheekTony Bennett, Lady Gaga2rank/position

Here is a duet by Tony Bennett, a true titan among titans in the jazz vocal world, and Lady Gaga, who can master any genre.
The song is “Cheek to Cheek,” a jazz standard cherished and sung by countless artists.
The lyrics say that being with you makes me feel as happy as if I were in heaven—and singing with Tony might just make you feel that way.
As time goes byTony Bennett3rank/position

Tony Bennett is a singer from the United States.
Alongside Frank Sinatra, he is a leading figure in show business and remains active on the front lines today.
On his 1970s album, The Great American Songbook—which features only American standards—you can hear As Time Goes By, the insert song from the film Casablanca.
Silver BellsTony Bennett4rank/position

When the Christmas season draws near, the atmosphere of the city seems to change and come alive, doesn’t it? A perfect song for this time of year would be this number sung by Tony Bennett.
It’s included on his 2008 album “A Swingin’ Christmas,” featuring a collaboration with the Count Basie Big Band.
The powerful sound of the big band and Bennett’s warm vocals blend beautifully, painting an urban yet heartwarming Christmas scene.
Nominated at the 52nd Annual Grammy Awards, this work is recommended not only for jazz lovers but also for anyone who wants to enjoy a calm, relaxing Christmas.
Why not play it as background music for those special moments with someone dear to you?
Stranger in paradiceTony Bennett5rank/position

It’s a popular song that has been covered by various artists.
The melody of this song is quoted from the classical piece “Polovtsian Dances” composed by Alexander Borodin, and the release of this song brought renewed fame to “Polovtsian Dances.”
The Shadow of Your SmileTony Bennett6rank/position

This is a song composed as the theme for the 1965 film The Sandpiper, starring Elizabeth Taylor and Richard Burton.
While the film itself didn’t make much of a splash, the song was well received and won the Academy Award for Best Original Song that same year.
Tony Bennett, who performed it, also won a Grammy Award.
The Way You Look TonightTony Bennett7rank/position

Tony Bennett, one of the greatest singers representing 20th-century America.
Among his many masterful performances, this is a work you’ll want to savor on a long autumn night.
Its supreme charm lies in a romantic worldview that celebrates the beauty found in a loved one’s unassuming gestures.
The gentle gaze that even finds endearment in moments of sadness seems to warmly envelop the listener’s heart.
This song was included on his 1958 album “Long Ago and Far Away,” and has been re-recorded several times since.
Notably, it gained recognition for its use in the 1997 film “My Best Friend’s Wedding.” It’s a perfect track for the chillier season, ideal for moments spent thinking of someone special.





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