The unlikely musical duo toured the world and released two Grammy-winning albums together, ‘Cheek to Cheek’ and ‘Love for Sale’

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 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 in February 2015.LARRY BUSACCA/GETTY

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 Stevie Wonder as well as a piano version of “Bad Romance.”

His milestone birthday was also commemorated with an NBC tribute special titled Tony Bennett Celebrates 90: The Best Is Yet to Come, filmed at Radio City Music Hall, where Gaga delivered a solo version of “The Lady Is a Tramp.”

Tony Bennett and Lady Gaga.CHRISTOPHER POLK/WIREIMAGE

“What a talent,” Bennett told Billboard of Gaga in 2016. “She knows how to perform well, and she’s just a great artist and a great person also. She has a lot of heart and a lot of soul, and she plays beautiful piano. She’s very accomplished as a performer. I think for the rest of our lives she’ll do wonderful things for us.”

Bennett was diagnosed with Alzheimer’s disease the same year, he revealed to AARP Magazine in 2021. In the outlet’s cover story about his experience with the disease, his eldest son Danny recalled a conversation with Gaga about revealing his diagnosis publicly.

“I wanted to check with her to make sure she was cool,” he told the publication, “because she watches his back all the time. She was like, ‘Absolutely, it’s just another gift that he can give to the world.'”

 Tony Bennett Still Recognizes Lady Gaga After Alzheimer’s Diagnosis: ‘She’s Hard to Forget’

Tony Bennett and Lady Gaga.KEVIN MAZUR/GETTY

At the time, Bennett’s wife Susan Benedetto also revealed that he still remembers Gaga. “Yes, but you know, Gaga is wonderful,” she said on CBS This Morning. “Most definitely. Gaga is hard to forget.”

That year, Bennett and Gaga teamed up for their second collaborative album, a Cole Porter tribute called Love for Sale. “The day we released ‘Cheek to Cheek’ in 2014, @itstonybennett called me and asked me if I wanted to record another album with him, this time celebrating the songs of Cole Porter,” she wrote on Instagram upon its announcement. “I’m always honored to sing with my friend Tony, so of course I accepted the invitation.”

Ahead of the album’s release, the pair performed two concerts at Radio City Music Hall to celebrate Bennett’s 95th birthday, billed as “One Last Time: An Evening with Tony Bennett & Lady Gaga.”

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In a memorable moment from one of the concerts, Bennett remembered his old friend, as she came out onto the stage. Of the emotional moment, Gaga shared on 60 Minutes, “That’s the first time that Tony said my name in a long time. I had to keep it together because we had a sold-out show and I have a job to do. But I’ll tell you when I walked out on that stage and he said, ‘It’s Lady Gaga,’ my friend saw me. It was very special.”

Love for Sale received six nominations at the 64th Grammy Awards, and Gaga wrote on Instagram that she was “stunned and shocked and beyond grateful” for the recognition at the time.

“This album happened because it was Tony’s idea and I made him a promise that we would make it and we did. At 95 years old, he has more nominations than ever, I’m so honored to be his companion in music and his friend,” she explained.

 Lady Gaga Performs Heartfelt Tony Bennett Tribute at the 2022 Grammy Awards: ‘I Love You Tony’

Tony Bennett and Lady Gaga in October 2015.D DIPASUPIL/GETTY

“Thank you to the public for loving us, we surely love each other, and you,” continued Gaga’s Instagram caption. “Believe in love and partnership, even with 60 years between us, and Alzheimer’s, there is nothing like the magic of music. I love you Tony, and the world loves you too. How could they not?”

After the nominations were announced, Gaga appeared on BBC Radio 2’s The Zoe Ball Breakfast Show to talk about Bennett following his Alzheimer’s diagnosis.

“Tony is one of my most favorite people on the whole planet and I love him with all my heart. I love his family with all my heart, I love his wife, Susan, with all my heart. I can’t tell you how much I learned from him and what it’s like to sing with a legend for so many years,” she told the program.

Lady Gaga and Tony Bennett in August 2016.DESIREE NAVARRO/FILMMAGIC

Gaga continued, “I’ve sung with Tony for almost 10 years, and it’s heartbreaking to watch what he’s going through having Alzheimer’s, and also I wish to say to anybody that’s listening that knows somebody with Alzheimer’s or dementia that’s dealing with that in their lives.”

“If you are with that person that you love, play some music from their childhood and I promise you that they will come to life in a way that is not expected, and not everyone you know, every case is different and everybody’s different, but they’re still there and my heart goes out to you and this album was made while he had Alzheimer’s and we sang it while he had Alzheimer’s and he were still able to do it, I am just floored by him,” she said.

Love for Sale won best traditional pop vocal album at the 2022 Grammy Awards ceremony, where Gaga performed solo versions of the album’s title track and “Do I Love You” as videos of their friendship played in the background.

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“I love you Tony, we miss you,” she said after concluding the performance.

Last week, Bennett paid tribute to Gaga for the last time with a sweet post on Instagram featuring the pair singing their version of Bennett’s “Night and Day” hit, originally off his Perfectly Frank album released in September 1992.

“Remembering the musical magic made in the studio with the remarkable Lady Gaga for our rendition of ‘Night and Day’,” he captioned the video.