More than a decade ago, and turned an unlikely musical pairing into a lasting and collaborative friendship.
The jazz legend, who 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 , 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 in 2014, recalling the evening. “Tony heard me sing it, and he asked to meet me after the show.
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 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."
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).
"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.
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.”
In promotion of the album, Bennett and Gaga embarked on the Cheek to Cheek Tour across North America and Europe throughout 2014 and 2015. They also performed the album's title track at the 57th Annual Grammy Awards, during which they won best traditional pop vocal album.
Bennett celebrated his 90th birthday in 2016 with a star-studded party at New York City’s famed Rainbow Room. Gaga was in attendance and presented him with a birthday cake, before taking the stage to perform “Signed, Sealed, Delivered I’m Yours" with as well as a piano version of "Bad Romance."
