More than a decade ago, Tony Bennett and Lady Gaga turned an unlikely musical pairing into a lasting and collaborative friendship.
The jazz legend, who died at age 96 on Friday after living with Alzheimer's disease since 2016, met Gaga in 2011 and quickly formed a close-knit relationship with the pop star, which resulted in two Grammy-winning duet albums: Cheek to Cheek and Love for Sale.
Their first encounter went down at the Robin Hood Foundation charity gala, where Gaga, 37, performed the jazz standard "Orange Colored Sky" and caught Bennett's attention. “We were fast friends – friends ever since [our first meeting],” she told PEOPLE in 2014, recalling the evening. “Tony heard me sing it, and he asked to meet me after the show. And I said, ‘Oh my gosh! Tony Bennett’s here!’”
Tony Bennett, Legendary Pop and Jazz Singer, Dead at 96
Tony Bennett and Lady Gaga onstage during the Stevie Wonder: Songs In The Key Of Life - An All-Star GRAMMY Salute held at Nokia Theatre L.A. Live on February 10, 2015
Tony Bennett and Lady Gaga in February 2015.
Michael Tran/FilmMagic
At the time, the "Bad Romance" singer-songwriter said she was "so nervous" to meet Bennett. “I fixed my hair, and my mom was fixing her makeup, and then we went back to meet him,” she explained. “He said, ‘Do you want to do a jazz album together?’ And I said, ‘Yes, of course I do!’”
Speaking to PEOPLE in 2016 about their initial meeting, Bennett said, "Ever since then, we've just been close. We just love performing with one another. She's terrific."
Later in 2011, he and Gaga collaborated for the first time on a cover of "The Lady Is a Tramp" from Babes in Arms for his album Duets II. Around its release, Bennett predicted Gaga would become as popular as Elvis Presley. "She is so spontaneous and improvised," he told ABC News at the time. "What's interesting about her, other than any person I ever met in the entertainment world, she changes from day to day."
How Lady Gaga and Tony Bennett Became 'Fast Friends'
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Three years later, the duo released their first collaborative album, Cheek to Cheek, a collection of compositions from The Great American Songbook including "Anything Goes," "I Can't Give You Anything But Love" and "It Don't Mean a Thing (If It Ain't Got That Swing)." Upon its release, Gaga told The Telegraph that she felt liberated by escaping pop music for a project to sing jazz with Bennett.
"He has made me so happy in the way that I really needed to feel. He’s really, like, saved my life," she told the outlet in 2014. "'Cause I really love music, and I really love being a singer, but I really hate being put in a box. And when I get put in a box I get very like a wild animal. And he let me be free. And I get to be with him while I’m doing it, and he’s teaching me all these life lessons, and I’m singing music I’ve loved my whole life. There’s no better music than the Great American Songbook. There just isn’t."
That year, their friendship also resulted in one of Gaga's tattoos. “I asked Tony to draw me a trumpet, and he sketched me Miles Davis’s trumpet. Then I had it tattooed with his last name, Benedetto, underneath,” she told PEOPLE at the time. “Just so I would always remember this time together.”
Lady Gaga and Tony Bennett's Friendship Through the Years
Tony Bennett and Lady Gaga perform onstage during The 57th Annual GRAMMY Awards at the STAPLES Center on February 8, 2015
Tony Bennett and Lady Gaga in February 2015.
Larry Busacca/Getty
"Remembering the musical magic made in the studio with the remarkable Lady Gaga for our rendition of ‘Night and Day’," he captioned the video.
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