In pop music history, collaborations have always been moments where worlds collide, either naturally or unexpectedly. They can surprise fans, spark reinventions, or simply be playgrounds for experimentation. There are countless iconic duets we still talk about today, but what I have been focusing on recently is another phenomenon I personally find fascinating:
That moment when a superstar with decades in the business teams up with an artist from a completely different generation, sometimes with a similar style, sometimes from a totally different genre. It’s the kind of pairing you’d normally expect only in fan fiction or a wild dream.
Whether it happens on stage or in the studio, these pairings always grab my attention. They show how past and present in music are constantly in conversation. Younger artists borrow sounds, styles, and even attitudes from their predecessors, while legacy acts feed off the fresh energy of the new generation, experiment, and reach audiences that weren’t even born when they first started making records.
Miley Cyrus, Lindsey Buckingham & Mick Fleetwood
The spark for this article came from Miley Cyrus’ recent release “Secrets” featuring Lindsey Buckingham and Mick Fleetwood. Two members of Fleetwood Mac (probably one of my favorite bands of all time) join Miley on a delicate, heartfelt tribute to her father, a gift she created for his birthday. Miley’s raw, tender vocals are wrapped in the warm texture of Fleetwood’s drums and Buckingham’s guitar. I immediately heard echoes of Fleetwood Mac’s 80s sound (Mirage, Tango in the Night) woven into the track.
And this isn’t even the first time Miley has teamed up with a Fleetwood Mac member. Remember the mash-up of Midnight Sky and Edge of Seventeen? Her 2020 lead single from Plastic Hearts blended seamlessly with Stevie Nicks’ 1981 hit.
Aerosmith & Yungblud
Another striking example: Aerosmith, a band that has been rocking since the early 70s, recently teamed up with Yungblud, born in 1997. Their song “My Only Angel” blends Aerosmith’s classic rock grit (think Dude [Looks Like a Lady], Sweet Emotion) with Yungblud’s raw, modern vocal production: compressed vocals, reverbs, and a touch of growl. Even though these two music worlds are a bit outside my usual listening, I found the result really interesting.
Here’s this kid that lives his life out loud… grew up on our records and the British invasion... and now we’re in the studio together creating something that bridges generations. He devoured all the same greats we looked up to… and then he started to dream on. It’s as simple as that.
Steven Tyler about Yungblud.
Damiano David, Tyla & Nile Rodgers
Who could’ve predicted Damiano David (Måneskin) and Tyla teaming up with Nile Rodgers? Their track “Talk to Me” mixes retro late ’70s funk, early 2000s pop energy, and a modern songwriting style. Rodgers, a true legend (founder of Chic, producer for Madonna’s “Like a Virgin”, Duran Duran “The Wild Boys” and “Notorious”, but also Daft Punk, and countless others), brings decades of history into the mix. What strikes me most is how, songs released more than 40 years ago, are still relevant for younger artists, who are turning to that sound to tell their own stories.
Dua Lipa & Cher
It’s not always about studio recordings. One viral moment that flooded my social media was Dua Lipa and Cher duetting on “Believe” at the Rock & Roll Hall of Fame. Zendaya introduced them on stage, a symbolic handoff across three generations of pop icons. The performance felt both unexpected and perfectly natural. This isn’t the first time Dua has performed with artists from different generations — or even in different languages. On her latest Radical Optimism Tour, she often invited special guests or covered songs by artists from the country or city she was in. As an Italian, I couldn’t miss her Italian-language tribute to national legend Raffaella Carrà, and honestly, it was incredibly well done. She’s also recently performed with Chaka Khan and Lenny Kravitz, and covered a few other tracks I’ve mentioned earlier in this article, just to self-quote.
Olivia Rodrigo & Robert Smith
Finally, I couldn’t miss mentioning Olivia Rodrigo with The Cure’s frontman Robert Smith, performing the band’s classics Friday I’m in Love (1992) and Just Like Heaven (1987). The collaboration followed their joint performance during her headlining set at Glastonbury on June 29, 2025. On paper, it’s an unexpected pairing: a Gen Z pop superstar alongside an iconic figure from the ’80s goth-alt rock scene. But in practice, it worked beautifully. These are the moments that introduce young fans to whole new musical worlds, while also highlighting the influences that subtly shape Olivia’s own sound. After all, songs like vampire or teenage dream carry more than a little emotional drama straight out of The Cure’s playbook, don’t they?
In conclusion, I love these collaborations because they remind us that music is a constant exchange across time. When legends and new voices meet, the result is never just nostalgia: it’s something fresh, unexpected, and bigger than both.
