From Cheek to Cheek and Love for Sale to Bennett attending the Joanne world tour, EW looks back at one of music's sweetest — and most peculiar — creative pairings.
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One of the fondest celebrity-in-the-wild memories I have involves the late, great Tony Bennett and glistening booty shorts.

It was Aug. 28, 2017, at Citi Field in New York City. I was headed to my seat amid a sea of glitter-encrusted, leather-strapped, high-heeled attendees gathered and ready to watch Lady Gaga take the stage on the first of two Joanne world tour stops in her hometown when the crowd erupted with applause before the concert even began. I noticed fans — from short-short-clad gays to more modestly dressed (and noticeably older) folks stand up to clap in unison. I whipped around, and my eyes locked with a very excited Bennett, who waved to an impromptu welcoming committee of disparate backgrounds, united in their enthusiastic greeting. He stuck around for a while, smiling and waving to his adoring public, and ultimately settled in a folding chair roughly 10 feet away from me for the remainder of the show.

Lady Gaga and Tony Bennett perform onstage in support of their award winning album "Cheek To Cheek"; Lady Gaga and Tony Bennett Love For Sale; "One Last Time: An Evening With Tony Bennett and Lady Gaga"
Lady Gaga with her friend and collaborator Tony Bennett
| Credit: Kevin Mazur/Getty Images(2)

At first, the thought of Bennett — who was, at the time, one year into his Alzheimer's diagnosis, though it hadn't been publicized yet — watching his Cheek to Cheek album partner gyrate and sing about masturbation on the Joanne tune "Dancin' in Circles" felt comical, so I made a mental note to keep tabs on Bennett during the performance. As Gaga powered through "Just Dance," he shimmied in his seat; during "Poker Face," he smiled. After "Applause," he applauded. Seeing Bennett as a Little Monster — the name Gaga has used for her fanbase since the beginning of her career — felt right in that moment, and I couldn't help but see the act of the audience clapping for Bennett's arrival earlier in the show as something altogether more powerful, and indicative of the importance of their creative entanglement.

They first worked together in 2011, at the height of Gaga's oddball empirical era, following the release of her pop culture magnum opus Born This Way, which had, months before, sold more than 1 million copies in its opening week. That made her appearance on Bennett's jazz-heavy Duets II album — with them covering Mitzi Green's 1937 song "The Lady Is a Tramp" — feel all the more shocking. No one could have predicted that one of the biggest names in modern pop would join forces with an octogenarian, especially one with whom most youngsters in Gaga's radical-youth fanbase likely had only a peripheral familiarity.

While "The Lady Is a Tramp" didn't exactly set the charts on fire (and, perhaps, was never intended to), it did lay a critical foundation for what would become one of the most significant steps in shifting Gaga's career from pop spectacle and to a focus on vocal prowess. Following the release of Born This Way, she faced a period of creative turmoil (another story for another piece) leading up to the unveiling of her 2013 album, Artpop, which aged better in retrospect versus how it landed at the time. Many called it a flop (despite its No. 1 debut and the birth of one of Gaga's biggest radio hits to date with its lead single, "Applause"). While Artpop's path to success was unclear, it was apparent that Gaga needed an aesthetic rehabilitation.

Enter Cheek to Cheek, a Grammy-winning full-length album composed of jazz standards sung by Gaga and Bennett, with solo numbers sprinkled throughout. Gone were Gaga's electro-heavy, bass-thumping bops; her showgirl bravado meshed with Bennett's classic, smooth, smoky vocals to create a most peculiar — but no less satisfying — marriage of unlikely styles that simply, inexplicably, worked. The album reached No. 1 in late 2014, and led to Gaga's showstopping Sound of Music medley at the 2015 Oscars. Suddenly, Gaga wasn't just a pop starlet — she was a respected vocalist, with Bennett guiding the way.

What could have ended there as a feather in Gaga's cap soon blossomed; the pair embarked on a 36-show Cheek to Cheek tour from 2014 to 2015 and released the PBS concert special Tony Bennett and Lady Gaga: Cheek to Cheek Live!

Unbeknownst to the public, Bennett was diagnosed with Alzheimer's in 2016, but Gaga continued to work with him throughout his later life. They recorded their second and final joint album, 2021's Love for Sale, between 2018 and 2020, and partnered on the emotional CBS special One Last Time, which chronicled their last onstage performance together in New York City.

Gaga regularly cried during the promotional cycle for the album, as she recounted savoring the moments of clarity she shared with Bennett as he lit up during their sessions together. His wife, Susan, even noted in a 2021 AARP profile that, while she misses the man she first fell in love it, "when he sings, he's the old Tony."

Gaga seemed to confirm this in an interview with Anderson Cooper, in which she spoke about escorting Bennett on and off stage for his final performances during their One Last Time concerts.

"I had to keep it together because we had a sold-out show, and I had 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, and it was very special," she told Cooper, later adding: "It's not a sad story. It's emotional. It's hard to watch somebody change. I think what's been beautiful about this, and what's been challenging, is to see how it affects him in some ways, but to see how it doesn't affect his talent. I think he really pushed through something to give the world the gift of knowing that things can change and you can still be magnificent."

It's fitting, then, that for a man whose talent was there for Gaga during the most trying period of her artistic career, she was the one to lead him off stage for the last time.

"Tony, we're all so grateful to have witnessed your talent, your generosity, your creativity, your kindness, and your service through all the years," Gaga said, taking his arm. "Mr. Bennett, it would be my honor to escort you off the stage," she finished, and walked with Bennett out of view to a thunderous standing ovation from the crowd at Manhattan's Radio City Music Hall.

The image is a powerful one, given Bennett's recent health struggles. It was a triumphant, celebratory end to a legendary story that could have been capped in sadness, but instead saw one of the industry greats bowing out with a contemporary mainstream pop staple at the top of her game.

Toward the end, both artists' followers most likely saw what they were intended to see in the fruits of the duo's relationship: an intergenerational connection of fanbases, musical styles, and unlikely celebrity chemistry that did what the best forms of entertainment do — entertain. But, tying it all together, the inexplicable, feel-it-in-the-air chill we all got witnessing two industry titans work their magic on stage was that feeling of closeness, intimacy, and genuine affection that kept Gaga and Bennett together for more than just a one-off promotional gimmick. When they were together, they were together. We weren't simply dazzled by the spark ignited by the juxtaposed spectacle of Lady Gaga singing with Tony Bennett — you always felt that, underneath it all, Anthony Dominick Benedetto saw Stefani Germanotta, whether he was next to her, in front of the cameras, taking the final bow of his career on a big-budget network concert special, or simply watching her — and only her — from a chair in the audience at the Joanne world tour.

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Related content:

Love for Sale (2021 album)

Lady Gaga and Tony Bennett follow up 2014's Cheek to Cheek with another jazzy collection, this time filled with Cole Porter cover songs.

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