For as fleeting as the music industry may be, the physical act of making music is a lifelong endeavor that commerciality has little to no control over, as proven by these four intergenerational musical collaborations.
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Indeed, maintaining top chart positions over decades is a rare feat. The long-time veterans who can say they’ve remained high on the charts for years on end often do so because of older albums that are still popular, not new music. But even as their mainstream popularity wanes, these musicians continue to hone and nurture their craft because that’s what musicians do.
As younger generations continue to enter the musical fold, more opportunities become available for these older, lifelong players to collaborate with their junior counterparts. Here are four of the best.
Mavis Staples and Jeff Tweedy
Mavis Staples got her start in her family band, The Staple Singers, which her father, Roebuck “Pops” Staples, established in the early 1950s. Jeff Tweedy of Wilco fame wasn’t even alive yet. Yet, despite their vast generational divide and stark difference in styles, the fellow Chicagoans started their intergenerational musical collaboration in the late 2000s.
“I come from the 1950s, so this isn’t supposed to be happening, Jeff Tweedy producing me,” Staples told the New York Times in 2010. “But after our first meeting, I felt like I knew him and was at ease and ready to go into the studio and make a good record. He looked out for me and kept me in my comfort zone. So, all of these songs are still Mavis and fit me like a glove.”
The pair worked together on three albums, including You Are Not Alone from 2010, One True Vine from 2013, and If All I Was Was Black from 2017.
Elton John and Brandi Carlisle
Whether she’s working with a reclusive folk icon like Joni Mitchell or a flamboyant rock pianist like Elton John, Brandi Carlisle is no stranger to intergenerational musical collaborations. The “You and Me on the Rock” singer first reached out to John via letter in 2009. Carlisle told John she had been a lifelong fan of his and asked him to play piano on one of her songs.
“The minute she arrived in the studio, I fell in love with her,” John recalled during a 2025 appearance on The Tonight Show with Jimmy Fallon. “And I fell in love with her talent, her voice. But more than that, I fell in love with the person. We’ve become firm friends, and we’re like family.”
Of course, as is often the case with family, things got contentious in the studio more than once. However, the pair rose above the challenges and released their first collaborative album, Who Believes in Angels?, in the spring of 2025.
Santana and Rob Thomas
Carlos Santana might have played an integral role in the development of late 1960s rock ‘n’ roll, but the 1990s were far less kind to the aging musician. Eager to find his way back into the mainstream, Santana began collaborating with Arista Records to find a younger pop musician who could work as a potential intergenerational musical collaboration.
EMI Music Publishing VP Evan Lamberg suggested Matchbox Twenty’s Rob Thomas. “Rob Thomas is the best songwriter I’ve ever signed,” Lamberg said, per Rolling Stone. “Rob just came off tour with Matchbox Twenty. He’s living at home with his fiancée and doing nothing except smoking pot and playing PlayStation. So, why don’t I send him the track and see what he thinks?”
Thomas and Santana did end up working together on the international 1999 hit, “Smooth”. As the last No. 1 hit of 1999 and first No. 1 hit of 2000, “Smooth” became the only song to appear on two decade-end Billboard charts. The song also won three GRAMMY awards.
Loretta Lynn and Jack White
Country music icon Loretta Lynn was in her early 40s when The White Stripes’ founder and multi-hyphenate musical icon Jack White was born. With such a wide age gap, it’s unsurprising that the pair’s intergenerational collaboration felt more like a mother-son relationship at times. Lynn and White began working together in the early 2000s, when White produced and performed on Lynn’s 2004 album, Van Lear Rose.
“I learned so much from working together,” White said in a statement after Lynn’s passing in 2022. “There was times where I just had to take a pause and step outside because she was just so brilliant, I couldn’t believe what I was witnessing and hearing. I almost felt like she didn’t even realize it. She was just a genius and brilliant at what she did. We were lucky to have her.”
The admiration was clearly mutual. During a 2005 appearance on 60 Minutes Uncut, Lynn and White talked about their collaborative and familial relationship. “I love you, baby,” Lynn told White as she patted his knee. “This is my baby,” she told the cameras, grabbing his hand with a smile.
Photo by Terry Wyatt/WireImage
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