Fans are mourning the incredible Tony Bennett, who died today at 96. One of the most impressive things about Bennett was how he continued to work and stay relevant for over 70 years, always winning over new generations of fans.

By appearing on MTV and collaborating with younger artists, Bennett was able to appeal to youth without ever changing the musical style that made him famous.

Perhaps his most famous was his collaboration with pop star Lady Gaga. Gaga, with her electronic-fused pop hits like “Just Dance” and “Poker Face,” may have once seemed like an unlikely duet partner, but the two formed a loving friendship that defined the last years of Bennett’s long career.

Read more about their inspiring collaboration.

Tony Bennett: working with younger stars

Tony Bennett began his career at a time when popular music was dominated by crooners, big bands and American jazz standards, and Bennett was one of this era’s top performers with hits like “Rags to Riches” and “I Left My Heart in San Francisco.” He was widely respected among his contemporaries, including Frank Sinatra, who once called him “the best singer in the business.”

But the type of music that made Bennett famous soon went out of fashion in favor of rock and roll. He struggled throughout the 1970s, by the decade’s end, he had no manager or recording contract, and developed a near-fatal cocaine addiction. But it was far from the end for Bennett.

His son Danny took over as his manager, and they mounted a comeback by trying to appeal to young people: Bennett would not change his old style but instead introduce younger audiences to the Great American Songbook.

Bennett appeared frequently on talk shows like Late Night with David Letterman. He even made appearances on MTV, and his MTV Unplugged special drew in a wide audience and won a Grammy Award, and featured collaborations with artists like Elvis Costello and k.d. lang.

“Tony Bennett has not just bridged the generation gap, he has demolished it,” the New York Times reported at the time. “He has solidly connected with a younger crowd weaned on rock. And there have been no compromises.”

In 2006, he released his platinum-selling Duets album, which featured collaborations from artists of many generations, including Barbra Streisand, Billy Joel, Elton John, Paul McCartney, Stevie Wonder, Sting, Bono Michael Bublé and John Legend.

Tony Bennett and Lady Gaga

But Tony Bennett’s most famous collaboration was with Lady Gaga. Despite their seemingly different styles and 60-year age difference, they formed an inspiring and successful duo.

Bennett and Gaga first met while both performing at a gala show in New York in 2011, where the pop star drew Bennett’s attention by singing jazz numbers — and he paid her a major compliment.

“I sang a couple jazz numbers that night, so I was real, real nervous to meet Tony Bennett — plus, I looked crazy,” Gaga recalled of their first meeting. “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. Bennett, and he said, ‘Lady, you are a jazz singer.’”

The two collaborated on Bennett’s follow-up album Duets II, and the crooner continued to be impressed with her talent.

“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,” he told Rolling Stone in 2012. “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.”

The two decided to record an album together. They released Cheek to Cheek, an album of jazz standards, in 2014 to great success: it debuted at #1 on the Billboard 200 Albums and won the Grammy Award for Best Traditional Pop Vocal Album. Gaga became the first woman to have three number one albums in the 2010s, while Bennett became the oldest artist ever to have a number one album.

The two also toured together and had a televised concert special. Through it all, they not only became great duet partners but great friends.

“I think something I was craving for myself was a truly authentic collaboration, a true artistic exchange,” Lady Gaga told Rolling Stone in 2015. “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.”

Gaga said that Bennett “saved” her when she was thinking of quitting music.

“Six months ago I didn’t even want to sing anymore,” she told Parade Magazine in 2014, saying that many people were taking advantage of her success. “I was so sad. I couldn’t sleep. I felt dead… And then I spent a lot of time with Tony. He wanted nothing but my friendship and my voice.”

“I tell Tony every day that he saved my life,” she said.

After working on separate projects for several years, Tony Bennett and Lady Gaga reunited for another collaboration — though this time it was much more bittersweet.

Bennett was diagnosed with Alzheimer’s in 2016, though the disease progressed slowly enough that he was able to continue on for a few more years. With the end in sight, he reunited with Gaga for what would be his final album and concert.

Bennett and Gaga performed together at Radio City Music Hall in New York City in a sold-out, two-night concert event that marked Bennett’s 95th birthday. It also proved to be his final performance: Bennett announced his retirement from touring shortly after.

They recorded a second duets album Love for Sale, which solely featured songs by Cole Porter. Released in September 2021, it was another hit, charting in the top 10:

Bennett broke the Guinness World Record as the oldest person to release an album of new material, and he also had the longest span of top-10 albums of any living artist.

The album won the Grammy Award for Best Traditional Pop Vocal Album and Best Engineered Album, Non-Classical, and was also nominated for Album of the Year.

While Bennett could not be there, Lady Gaga performed two of the tracks live at the ceremony and ended with a sweet tribute to her friend and duet partner: “I love you Tony, we miss you.”

Tony Bennett and Lady Gaga may have once seemed like an unlikely pair but they proved to be a match made in heaven, giving Bennett an amazing partner in the final years of his career.

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