4 of the Best Intergenerational Collaborations Between Musicians From the 20th and 21st Centuries

The music industry and its biggest stars might be fleeting and fickle, but music as an art form is timeless and immortal. No facet of modern-day music proves the latter idea quite as convincingly as intergenerational collaborations that see musical stars from the 1960s teaming up with modern-day artists who reached their professional peak post-Y2K.

Not every collaboration that spans multiple generations is a guaranteed classic. Sometimes, differences in creative styles make for a clunky mash-up. These four intergenerational collabs, however, take the best elements of both artists and create something entirely new.

“Little Bit” by Mavis Staples feat. Jeff Tweedy

Long before Jeff Tweedy was a twinkle in his father’s eye, Mavis Staples was establishing a successful career with her family band, The Staple Singers, out of Chicago, Illinois. Decades later, Tweedy would do the same thing with his various projects out of the Windy City, including Wilco, Uncle Tupelo, and his own family project, Tweedy.

Tweedy and Staples have joined forces several times since the 2010s, but one of their best joint efforts is undeniably “Little Bit” off Staples’ 2017 album, If All I Was Was Black. The message, Staples’ vocal delivery, that nasty guitar riff: it’s a masterclass in intergenerational groove.

“Every Planet We Reach Is Dead” by Gorillaz feat. Ike Turner

Ike Turner was on the front lines of the early rock ‘n’ roll movement of the 1950s and 60s. Half a century later, he was on the front lines of early-2000s alt-rock alongside the Damon Albarn-led virtual band, Gorillaz, playing keys on “Every Planet We Reach Is Dead” from Demon Days.

Albarn met Turner while living in California, and the pair’s frequent conversations about music naturally led to their collaboration. Speaking to the Associated Press in 2005, Albarn said the idea to include Turner was “kind of [a] light bulb moment…he just did his thing on it…and it turned out great.”

“Please Please Please” by Sabrina Carpenter feat. Dolly Parton

Differences in musical style and upbringing aside, Sabrina Carpenter and Dolly Parton have a lot in common. Both are incredibly talented soprano songwriters who have built their careers playing up the hyper-sexual, hyper-blonde stereotype to their own advantage.

So, it’s only natural that the two light-haired ladies would join forces on a rendition of Carpenter’s country-tinged heartbreak song, “Please Please Please”. The version with Parton has noticeably fewer F-bombs, per Parton’s request. Still, this intergenerational collaboration is proof of two things. One, country and pop go together like sequins and lamé. And two, no matter if it’s the 1960s or the 2010s, sex sells, plain and simple.

“I Get A Kick Out Of You” by Tony Bennett and Lady Gaga

Whereas some intergenerational collaborations only last for a song or two, Lady Gaga and Tony Bennett released two full-length studio albums, Cheek To Cheek and Love For Sale, in 2014 and 2021, respectively. The collab was symbiotically beneficial, introducing Bennett to a new, younger audience and giving Gaga a chance to show off a different side of her vocal abilities.

The pair’s version of Cole Porter’s “I Get A Kick Out Of You” came from the latter LP, Bennett’s last album, as the iconic crooner died in 2023. His and Gaga’s collaborative albums remain an impressive part of Bennett’s larger musical legacy.

Photo by Tim Mosenfelder/Getty Images

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