Tony Bennett Popular Song Rankings [2025]

Winter WonderlandTony Bennett8rank/position

Tony Bennett – Winter Wonderland (from A Swingin’ Christmas)

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 Evans9rank/position

Tony Bennett & Bill Evans – Maybe September

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!

Love Is Here To StayTony Bennett & Diana Krall10rank/position

Tony Bennett, Diana Krall – Love Is Here to Stay

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!

You Must Believe In SpringTony Bennett & Bill Evans11rank/position

You Must Believe In Spring – Tony Bennett and Bill Evans

Tony Bennett, a popular music singer who was active from the 1950s to the 1960s, was so highly regarded that Frank Sinatra called him “the best singer in the world.” Even during the heyday of rock, his steady vocals kept him in the spotlight among many listeners.

A collaboration he did with the world-renowned jazz pianist Bill Evans is the work You Must Believe in Spring.

With melodies and lyrics themed around spring, it became a beloved classic in many countries.