From Frank Sinatra to Lady Gaga: Tony Bennett’s greatest duets

The death of Tony Bennett, one of the most beloved singers of all time, leaves behind a stacked discography of some of the greatest covers in the Great American Songbook. But while Bennett was no doubt a towering artist on his own, his expansive career was expertly accented by a penchant for collaboration. Whether through his two massively successful Duets albums which featured Bennett alongside a host of artists, or through his award-winning partnerships with everyone from Lady Gaga to Diana Krall as well as a spate of one-offs, Bennett clearly relished sharing the stage with mentors, mentees and contemporaries alike. Sifting through a seven-decade discography, here are a few of some of the icon’s best duets throughout a gold standard career.

I Left My Heart in San Francisco with Judy Garland

Only a talent like Judy Garland can invigorate what would become a trademark tune of Bennett’s career. By the time the two joined forces on I Left My Heart in San Francisco for a 1963 episode of The Judy Garland Show, the song was already a smash. In the hands of the two legends, it leapt into the stratosphere; a mutual respect apparent. “One of the best compliments I ever received was from Judy,” Bennett wrote in his 2012 book Life is a Gift. “She said that I was the epitome of what entertainers were put on earth for.”

New York, New York with Frank Sinatra

Frank Sinatra once called Tony Bennett his favorite entertainer, a stamp of approval that lasted for the entirety of Bennett’s career. The two were indelibly linked: dynamite vocalists who exuded class, were larger than life and championed great music. While the two legends collaborated a variety of times (check out their swingin’ version of the Chicago ode My Kind of Town) their most notable duet is on a song about another town they’re both most linked to. Jersey-born Sinatra famously dreamt of the Big Apple and first shot to fame there, while Bennett was born in Queens and spent the majority of his life in Manhattan, over the years delivering memorable performances at both Carnegie Hall and Radio City (where he took his final bow in August 2021). That backstory makes the triumphant lyrics to the Theme from New York New York that much more meaningful.

Cheek to Cheek with Lady Gaga

It was a partnership that forever altered the career of the two musical icons. For Gaga, her association with Bennett gave her an air of gravitas, allowed her to explore an entirely new aspect to her artistry and helped prove she wasn’t just a dance-pop act known for outrageous outfits. For Bennett, Gaga helped introduce the legend she so revered to a new generation of fans, and delivered one final triumphant chapter of a decades-spanning career. The bond the two shared has been oft-discussed, and it all started with this title track of their first album together of standards from the Great American Songbook

Body and Soul with Amy Winehouse

Four months before the tragic death of Amy Winehouse in July 2011, her final-ever recording session was with Bennett for his Duets II album. Winehouse grew up with a passion for crooners like Bennett and the aforementioned Sinatra, and the two enjoyed a mutual respect for each other. “She said she was nervous because she had never recorded a song with someone she considered one of her idols,” Bennett later recalled. “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.” The vocals Winehouse delivers, perhaps reminiscent of Billie Holiday, showcase that raw emotion.

Love is Here to Stay with Diana Krall

In the midst of the final decade of Bennett’s life, the artist not only recorded with Gaga but enjoyed a fruitful collaboration and kinship with fellow jazz great Diana Krall. In 2018, the two teamed up for Love is Here to Stay; a tribute to the songwriting greats George and Ira Gershwin, with Bennett and Krall delivering a definitive version of the titular American standard. Clocking in at over four minutes, the two take their sweet time to equally delicious results, from its little-heard introduction to a brilliantly understated ending. What we wind up with is one of the greatest love songs ever written courtesy two artists at the top of their game.

Young and Foolish with Bill Evans

By the 1970s, Bennett experienced a sad lull; the sounds of swing and jazz simply weren’t cool any more and Bennett’s personal life was in disarray thanks to a crumbling marriage and a drug habit. One of the few bright spots of this era is his collaboration with the pianist Bill Evans; the two stripped away the sound of a large band and simply zeroed in on Bennett’s voice and Evans’s lush virtuosity on the piano. The pair recorded two exemplary albums, one of which included the standout Young and Foolish. It’s a cover of a fluffy show tune from the obscure 50s-era musical Plain and Fancy, transformed here into an emotionally powerful musing. By 1980, Evans would be dead of a drug overdose; while Bennett would go on to pick up the pieces of his life and reinvent himself once more.

Don’t Get Around Much Anymore with Michael Bublé

Aside from the aforementioned Gaga, Bennett influenced a host of modern singers; teaching them about his passion for the Great American Songbook and laying a blueprint as to how to navigate life as a classic crooner. One of his many disciples, Michael Bublé grew up listening to the legend, modeling much of his career after him. Their joint charisma shines on Don’t Get Around Much Anymore, a song that while boasting melancholy lyrics, comes across downright joyful thanks to their vocal prowess.

Smile with Barbra Streisand

Known for her own string of duets, Barbra Streisand joined with Bennett to take on this Charlie Chaplin-written classic for his debut Duets album. Accompanied by glistening piano, Bennett starts out subtly before Streisand joins in on the second verse. By the last line when the two simultaneously sing “When you just smile,” you know you have just heard something special.

How Do You Keep the Music Playing with Aretha Franklin

From Bennett’s second Duets album, How Do You Keep the Music Playing tells the tale of the smoldering embers of a long relationship; posing that all-too important question of how one makes it last. It’s only fitting that he’s alongside the Queen of Soul herself as the two trade their unmistakable vocals. Aside from the expert deliveries by the two late legends, if the lyrics sound painfully truthful perhaps that’s also because they were written by the dynamic married songwriting duo: Alan and Marilyn Bergman.

I’ve Got You Under My Skin with Lady Gaga

For what would become the final album Bennett recorded, he teamed up with Gaga for the Cole Porter-tribute Love for Sale on which the two energetically have a blast on the peppy I’ve Got You Under My Skin, a song perhaps made most famous by Sinatra. For Bennett, the song and album turned out to be a perfect bow. By the time of his final-ever performance at Radio City Music Hall in August 2021, Bennett was in the midst of Alzheimer’s and Gaga proved to be the perfect partner as he took the stage, and gracefully helped usher him off into the annals of music history.