The Best Surprise Concert Guests of Summer 2025

GLASTONBURY, ENGLAND - JUNE 29: Olivia Rodrigo performs with Robert Smith (R) onstage during day five of the Glastonbury Festival 2025 at Worthy Farm, Pilton on June 29, 2025 in Glastonbury, England. Established by Michael Eavis in 1970, Glastonbury has grown into the UK's largest music festival, drawing over 200,000 fans to enjoy performances across more than 100 stages. In 2026, the festival will take a fallow year, a planned pause to allow the Worthy Farm site time to rest and recover. (Photo by Kevin Mazur/Getty Images for Olivia Rodrigo)


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.