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The Best Surprise Concert Guests of Summer 2025

If you’re a pop star with a big show, why not make it even bigger by bringing out one of your all-time heroes?


This summer, there’s no pop star accessory like a legendary onstage guest. A-listers from Olivia Rodrigo to Sabrina Carpenter to Gracie Abrams to Drake have scored some of 2025’s most talked-about moments by bringing out one of their all-time heroes for a very special duet at whatever festival or mega-show they’re headlining that night. (Earlier in the year, several artists at Coachella arguably got this trend started for 2025, and Janelle Monáe and Grace Jones extended it to a whole co-headlining concert in June.) At their best, these surprise inter-generational collaborations feel genuinely awesome, and if you’re lucky enough to be in the crowd when one happens, you’ll be bragging to your friends for months. Here are 10 of the best unannounced music-legend pop-ups we’ve seen lately.

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