Tony Bennett's Most Popular Songs Ranking [2026]
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.
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Tony Bennett Popular Songs Ranking [2026] (1–10)
The Way You Look TonightTony Bennett8rank/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.
Winter WonderlandTony Bennett9rank/position
This song doesn’t mention Christmas in its lyrics, yet it always gets played during the holiday season.
The setting of the song is Central Park in Honesdale, Pennsylvania, a tourist spot known for offering various recreational activities.
It’s performed by the legendary singer Tony Bennett.
Maybe SeptemberTony Bennett & Bill Evans10rank/position
The work “Maybe September,” a collaboration between Italian-American vocalist Tony Bennett and world-renowned jazz pianist Bill Evans.
Tony Bennett is often hailed as one of the greatest entertainers in the world, making this a collaboration widely recognized as a major event by both fans and the artists themselves.
The melody is slow jazz, arranged to spotlight Bennett’s rich, resonant vocals.
It’s a perfect piece for an autumn evening!
Tony Bennett Popular Song Rankings [2026] (11–20)
Love Is Here To StayTony Bennett & Diana Krall11rank/position
Composed by the great American songwriter George Gershwin together with his lyricist brother Ira Gershwin, this is a timeless jazz standard that has been loved across generations.
Among the many outstanding covers by renowned singers, today I’d like to highlight the duet version by living jazz legend Tony Bennett and popular jazz vocalist Diana Krall.
Featured as the title track on their 2018 album Love Is Here to Stay, which focuses on the works of the Gershwin brothers, it boasts an elegant, refined arrangement and truly superb performances by these two great artists.
Not just this song, but the entire album is perfect for long autumn evenings—so don’t stop at a single track; give the whole album a listen!
