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Stories

Tony Bennett’s Greatest Duets From Judy Garland To Frank Sinatra

by Peace A • Published July 27, 2023

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Tony Bennett's Greatest Duets
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Tony Bennett left behind a great deal of artistry and iconic musical work, including collaborations with other amazing music artists. His flair for partnership not only established great relationships for the late singer, but is also a reason for his tremendous success in the American music industry.

From award-winning duets with Lady Gaga to Diana Krall, Tony’s performances will be greatly missed. Music stars and celebrities have come out on social media to mourn the loss of their dear friend. Here are some of Tony’s memorable duets throughout the years.

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“I Left My Heart in San Francisco” with Judy Garland

Tony Bennett's Greatest Duets
Youtube video screenshot

On a 1963 episode of The Judy Garland Show, Tony and Judy serenaded the audience with a joint performance of Tony’s trademark tune—”I Left My Heart in San Francisco.” Tony referred to Judy in his 2012 book Life is a Gift. “One of the best compliments I ever received was from Judy. She said that I was the epitome of what entertainers were put on earth for,” he wrote.

RELATED: Tony Bennett Says His Greatest Regret Was Not Warning Amy Winehouse Of The Dangers Of Drugs

“Love is Here To Stay” with Diana Krall

In 2018, Tony teamed up with fellow jazz star Diana Krall for a definitive version of “Love is Here to Stay” — a tribute to the songwriters George and Ira Gershwin. The duet is regarded as one of the greatest love songs ever written and was beautifully rendered by both music icons.

“New York, New York” with Frank Sinatra

Frank Sinatra idolized Tony as his favorite entertainer, and they collaborated multiple times, with their most notable duet based in New York. Both singers share the sentiment about New York, as Sinatra first had his shot to fame in the city, and Tony spent most of his life in Manhattan; their shared experience birthed the lyrics to the theme from “New York, New York.”

His Many Heartfelt Duets with Lady Gaga

Tony Bennett's Greatest Duets
Youtube video screenshot

Lady Gaga and Tony’s duets are among the most memorable, with clips making rounds on social media after his death. Their relationship was symbiotic, helping Gaga explore a new side to her music, and Bennett getting exposed to a new generation of fans.

They made two albums — Cheek to Cheek in 2015 and Tony’s final album, I’ve Got You Under My Skin, in 2021. His last ever performance was also with Gaga at Radio City Music Hall in August 2021. Tony was battling Alzheimer’s then, but this never affected his performances.

“Body and Soul” with Amy Winehouse

Tony Bennett's Greatest Duets
Youtube video screenshot

Amy Winehouse had her last recording session with Bennett for his Duets II album in 2011. Sadly, she died four months later, which was devastating to Tony and her fans worldwide. “She said she was nervous because she had never recorded a song with someone she considered one of her idols. After running through a few bars, she said she hadn’t recorded for a long time – her only reference to the problems she’d been living through,” Bennett had said, recalling the moment.

“Smile” with Barbra Streisand

Barbra Streisand is famous for duets, and she joined Tony on “Smile,” a Charlie Chaplin-written classic for his debut Duets album. Accompanied by piano, Tony takes the lead before Barbra joins in the second verse. They both end with the line “when you just smile” in blissful harmony.

“How Do You Keep The Music Playing” with Aretha Franklin

Tony Bennett's Greatest Duets
Youtube video screenshot

Aretha Franklin featured “How Do You Keep The Music Playing” on Tony’s Duets II album. The song tells the story of a long-term relationship and how one makes it last. The song was written by songwriting duo Alan and Marilyn Bergman, given even more meaning to the music brilliantly delivered by Tony and Aretha.

“Young and Foolish” with Bill Evans

tony bennett bill evans
Youtube video screenshot

Tony recorded this song with Bill Evans during a tumultuous decade of his life. A new era in music was emerging, and swing and jazz were not in vogue anymore. Tony was also dealing with a crumbling marriage and drug addiction then; however, one of his most beautiful duets was birthed amidst this chaos.

Tony and Bill Evans recorded two albums, one of which was Young and Foolish. It was an emotional cover for the musical Plain and Fancy from the ’50s.

“Don’t Get Around Much Anymore” with Michael Bublé

Michael Bublé grew up listening to Tony and modeled much of his music career to his idols. Bublé got to duet with Tony on “Don’t Get Around Much Anymore.” Both classic and modern legends brought life and a joyful touch to the song’s melancholy lyrics.

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