Tony Bennett, who died today at the age of 96, was a singular figure in music — a classic crooner who weathered the fickle winds of popular music over multiple decades by adapting but never fundamentally changing who he was. His initial rise and success were astounding in their own right, but the second half of Bennett’s career is just as fascinating. Starting in the Nineties, Bennett didn’t so much try to court younger audiences or artists but find some kind of common ground with them.
There was his acclaimed MTV Unplugged from 1994 — featuring k.d. lang and Elvis Costello — and his two Duets albums in 2006 and 2011, which featured fellow legends both old (Barbra Streisand, Paul McCartney, Elton John) and new (John Legend, Amy Winehouse, Norah Jones). And while Bennett released collaborative albums with other artists, like lang and Diana Krall, it was his musical relationship with Lady Gaga that defined the final decade of his career.
Bennett and Gaga first worked together on 2011’s Duets II, and over the next decade, they released two albums together, toured the world, and closed out Bennett’s career with a grand denouement at Radio City Music Hall. Below is a timeline celebrating their creative and personal relationship, as well as all the music they made together.
May 9, 2011: “Lady, you’re a jazz singer”
Gaga and Bennett first crossed paths at the 2011 Robin Hood Foundation gala in New York City, where both were performing. Gaga had performed a rendition of Nat King Cole’s “Orange Colored Sky,” and after the show, she was told Bennett wanted to meet her. As Gaga recalled at their final concert: “I sang a couple jazz numbers that night, so I was real, real nervous to meet Tony Bennett — plus, I looked crazy. I had blonde in my hair and black in my hair, red lipstick, I had four big velvet moles on my face. I was doing my thing. And I went to meet Mr. Benett, and he said, ‘Lady, you are a jazz singer.’”
Summer 2011: Duets II
Gaga and Bennett’s first song together was “The Lady Is a Tramp,” a Rodgers and Hart show tune from the 1937 musical, Babes in Arms. Recorded at Avatar Studio in Manhattan, the song eventually opened Bennett’s Duets II. Present at the recording session was the great journalist Gay Talese, who documented the entire proceedings for an article published in The New Yorker in September.
Dec. 12, 2011: “Why am I naked?“
A couple of weeks before the release of Duets II, Bennett put a nude sketch he made of Gaga during an Annie Leibovitz photo shoot for Vanity Fair up for auction. Earlier that year, on her Thanksgiving special, Gaga joked about the picture, saying, “I walked in and said, ‘Well, Tony, here we are,’ and I dropped my robe, and I got into position. I felt shy and thought, ‘It’s Tony Bennett. Why am I naked?’”
Jan. 11, 2012: As good as Ella and America’s Picasso
In an interview with Rolling Stone, Bennett spoke about working with Gaga on “The Lady Is a Tramp”: “She came in so prepared and so knowledgeable about what to do. She’s as good as Ella Fitzgerald or anybody you want to come up with. And that’s without her dancing and her philosophies about breaking myths that are incorrect and social situations. She’s very strong. I know it sounds way out, but she could become America’s Picasso if they leave her alone and let her just do what she has to do. She is very, very talented.”
Sept. 28, 2012: The collaboration continues
While promoting his multi-lingual Viva Duets project, Bennett broke the news to Rolling Stone that he and Gaga were planning to record an album together. “Of all things, she called me from New Zealand and said, ‘I want to do a jazz album with you,’” Bennett said. “We’re gonna do a jazz album with [composer] Marion Evans, a big swing band, and I’m looking forward to it because a lot of people don’t know it, but she’s a phenomenal jazz singer.”
Spring – Summer 2013: Cheek to Cheek sessions
The recording of Cheek to Cheek finally got underway during the spring and summer of 2013. Gaga later recalled her nerves at the time, saying, “I was so nervous to go into the studio with him, I just wanted him to hear I have an authentic jazz voice and that I studied that. “f he can hear that, I’m okay. If he can’t hear it, I’m not an authentic jazz voice.”
June 18, 2014: Tattoo you
One of Lady Gaga’s latest tattoo? A sketch of Miles Davis’ trumpet, drawn by Bennett himself.
July 29, 2014: “Anything Goes”
After nearly two years of waiting, Gaga and Bennett officially announced Cheek to Cheek and shared the first single, a version of the Cole Porter classic, “Anything Goes.” Coinciding with the album announcement, the pair took the stage at the Rose Theater at Lincoln Center in New York for a performance that was recorded and later released as Tony Bennett and Lady Gaga: Cheek to Cheek Live!
Ahead of the concert, Bennett and Gaga teased the album to Rolling Stone, with Bennett saying, “It’s all the great songs of George Gershwin, Cole Porter, Irving Berlin, all the greatest composers. No other country has ever given the rest of the world so many magnificent songs, and they’re gonna live forever. Wait ’til you find out when she sings those songs.”
Gaga added: “He wanted me to sing a lot of different songs. He really likes when I sing [Billy Strayhorn’s] ‘Lush Life.’”
Aug. 26, 2014: Behind the scenes
Ahead of the release of Cheek to Cheek, Gaga and Bennett shared a music video for their take on “I Can’t Give You Anything But Love,” which featured a ton of behind-the-scenes footage from the studio sessions.
Sept. 19, 2014: Number One
Cheek to Cheek arrived and debuted at Number One on the Billboard 200 Albums chart, selling 131,000 copies in its first week.
December 2014: A very good year
Gaga and Bennett capped off their big year together with a string of memorable performances. Early in the month, they stopped by The Tonight Show for a mini set that included “Cheek to Cheek” and “It Don’t Mean a Thing (If It Ain’t Got That Swing).” Gaga also delivered a solo rendition of Cole Porter’s “Every Time We Say Goodbye.” A couple of weeks later, they rang in 2015 with a special New Year’s Eve performance in Las Vegas.
Feb. 8, 2015: Grammy gold
At the 57th Grammy Awards, Cheek to Cheek was honored with Best Traditional Pop Vocal Album, while Gaga and Bennett also took the stage for a rendition of the title track. In an interview with Rolling Stone backstage that night, Gaga reflected on her creative partnership and friendship with Bennett: “I think something I was craving for myself was a truly authentic collaboration, a true artistic exchange,” she said. “With Tony I found not only that, but I found a friend. Not only do we spend a lot of time together and make music, but we talk. It’s been an incredible experience all the way around.”
April to August 2015: On the road
Gaga and Bennett took Cheek to Cheek on the road, embarking on an extensive tour that included dates across North America and Europe.
Dec 16. 2016: An all-star tribute
Lady Gaga joined Billy Joel, Elton John, Diana Krall, k.d. lang, Stevie Wonder, and many more for a tribute concert celebrating Bennett’s 90th birthday. Gaga fittingly performed the first song she and Bennett recorded together, “The Lady Is a Tramp,” and also performed a rendition of the Édith Piaf’s “La Vie en Rose.”
Feb. 1, 2021: Bittersweet reunion
After the whirlwind Cheek to Cheek era, Bennett and Gaga went their separate ways for a few years. Bennett continued to tour and released a collaborative album with Krall, Love Is Here to Stay, in 2018; and Gaga did Gaga, dropping Joanne in 2016 and Chromatica in 2020, while launching her acting career with A Star Is Born and House of Gucci as well. Word that the pair had reunited and recorded a new album finally arrived in 2021 — but it was accompanied by the news that Bennett was battling Alzheimer’s disease.
According to an AARP Magazine story at the time, Bennett and Gaga recorded the Cheek to Cheek follow-up between 2018 and 2020, as Bennett’s Alzheimer’s was progressing. Bennett’s son, and longtime manager, Danny Bennett, recalled speaking with Gaga about going public with the crooner’s diagnosis: “I wanted to check with her to make sure she was cool, because she watches his back all the time,” he said. “She was like, ‘Absolutely, it’s just another gift that he can give to the world.’”
Aug. 3 & 5, 2021: A birthday bash and a big goodbye
Gaga and Bennett took the stage at Radio City Music Hall for a pair of special reunion concerts. The two shows were meant to celebrate Bennett’s 95th birthday, but they also proved to be the crooner’s last live performances. A few days after the concerts, the singer’s family canceled his remaining shows for the year and announced that he would retire from touring. The Radio City concerts were filmed and later aired as a concert special, One Last Time: An Evening with Tony Bennett and Lady Gaga.
Sept. 30, 2021: Love for Sale
Gaga and Bennett released their second collaborative album — and Bennett’s final album — Love for Sale. Exclusively featuring songs from the Cole Porter songbook, the album is primarily comprised of duets, though it also features a few solo tunes from Gaga and Bennett.
Dec. 17, 2021: Unplugged (redux)
About a month before their Radio City Music Hall shows, Gaga and Bennett quietly recorded an intimate set for MTV’s long-running Unplugged series. The special finally aired in December, featuring performances of songs like “Night and Day” and I’ve Got You Under My Skin.”
April 3, 2022: A golden Grammy moment
Bennett and Gaga earned five Grammy nominations for Love for Sale, including nods for Album of the Year and Record of the Year for their rendition of “I Get a Kick Out of You.” The LP ended up taking home two awards, Best Traditional Pop Vocal Album, as well as Best Engineered Album, Non-Classical.
Gaga also took the stage solo for a special tribute to Bennett, performing “Love for Sale” and “Do I Love You” in his honor. Bennett even appeared in a pre-taped video to introduce the performance, while footage of the pair performing and recording together played behind Gaga as she delivered an emotional rendition of “Do I Love You.”
“I love you, Tony, we miss you,” Gaga said straight into the camera as the audience roared.
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