Best Surprise Guests at 2025 Concerts: Olivia, Sabrina, Drake

The legendary surprise that kicked off a summer full of ’em. Olivia Rodrigo’s headlining performance on the second night of Governors Ball was already one of the most fun, high-energy festival sets of the year — and then she brought out former Talking Heads frontman David Byrne for 1983’s “Burning Down the House.” Trading vocals on an absurdly catchy art-pop classic is one thing; nailing the synchronized choreography that goes with it is another. Rodrigo and Byrne did both to wild cheers from the all-ages crowd, grooving down the catwalk side by side as if they’d been performing together for years. “Holy shit, that was so cool,” she said as he left the stage. Couldn’t have put it better ourselves. —Simon Vozick-Levinson

Just a few weeks later, Rodrigo kept the excitement coming when she brought out Ed Sheeran at the London festival BST Hyde Park 2025. “He’s one of my favorite Brits and one of the best songwriters of all time,” she said before the pair broke into a lovely, acoustic rendition of Sheeran’s first-ever hit, “The A Team.” (Later, they also shared a quick TikTok mash-up of Rodrigo’s “Happier” and Sheeran’s “Perfect” that they’d recorded backstage.) Sheeran wrote about the experience in a heartfelt Instagram caption: “Been a fan of Olivia’s since Drivers License blew my mind back at the start of 2021…  I’m a proper fan. Was gonna go watch the show anyway but she hit me and asked to sing ‘The A Team’ with her, which was such a buzz. That song turns 15 this year, and I remember playing it to rooms with no one in it in 2010, so to still be playing it to new fans with one of the brightest stars of the next generation is an honour and a privilege.” —Maya Georgi

OK, now it’s official: Olivia Rodrigo is the new Queen of the Eighties. O-Rod spent her historic summer-festival rampage taking the stage to the Go-Gos’ “We Got the Beat,” but she really took the prize at Glastonbury, when she stunned the crowd by bringing out the Cure’s Robert Smith to duet on “Just Like Heaven” and “Friday I’m In Love.” Goth idea, right? “He’s perhaps the best songwriter to come out of England,” she announced. “He is a Glastonbury legend and a personal hero of mine!” Cure freaks everywhere loved seeing Robert have this much fun onstage, trading verses and grinning over at her as he sang, “I’ll run away with you!” She’s a longtime Cure superfan — who can forget the footage of teen Olivia in the car belting “Boys Don’t Cry”? — so both stars brought pure enthusiasm. She even posted a backstage photo of them doing shots together, which was so American of her. It was just like a dream. —Rob Sheffield

Halfway through her set at BST Hyde Park, Sabrina Carpenter had an unusual request for her audience: howl at the moon. Thousands of cries echoed beneath the London sky, as Carpenter stood smiling. “I’m going to need you guys to put that howling to good use,” she told the audience. Would this be a sultry cover of Ozzy Osbourne’s “Bark at the Moon?” A pop rendition of Warren Zevon’s “Werewolves of London?” Nope, even better: “Hungry Like the Wolf,” with a surprise appearance from Duran Duran themselves. Simon Le Bon showed up in his signature white blazer and traded vocals with Carpenter, with John Taylor on bass. If there’s one thing we know about Carpenter, it’s that she loves music history — and the Eighties are no exception. Here’s hoping she brings out Tears for Fears next. —Angie Martoccio

When Drake headlined all three nights of London’s Wireless Festival, it was an opportunity to show off some new moves and a new approach in the wake of a certain beef you may have heard about. It was also an opportunity to bring out a shitload of guests, including 21 Savage, Rema, Vanessa Carlton, Bryson Tiller, Givēon, and PartyNextDoor. Arguably the most exciting cameo, though, came from Ms. Lauryn Hill, who performed her 1998 classic “Ex-Factor.” The song segued into Drake’s “Nice For What,” the 2018 hit that samples “Ex-Factor,” providing a nice full-circle moment. The crowd loved it — which was especially good to see after delays at Essence Fest forced Hill to take the stage during the wee hours and perform to a nearly empty Superdome earlier in the month. 

Zach Bryan and Bruce Springsteen have appeared together before, including on the cover of Rolling Stone’s 2024 Musicians on Musicians issue, where Bryan talked about how he and his buddies like to go to bars and dial up “Born in the U.S.A.” a couple hundred times in a row on the jukebox. (“This is crazy, my man,” Springsteen replied.) This summer, when Bryan played three nights at New Jersey’s MetLife Stadium, Springsteen popped up again to duet on “Atlantic City” and Bryan’s own “Revival,” in a moment that reinforced the deep kinship they share as songwriters. Maybe it’s not exactly the world’s biggest surprise to see these two guys join together at this point, but it sure feels like the stuff of Jersey legend when they do. —S.V.L.

During Bleachers’ headlining set on the first night of this year’s Newport Folk Festival, Jack Antonoff brought out a stream of guests, including Hayley Williams, Jeff Tweedy, Weyes Blood, Waxahatchee, and folk singer Dan Reeder. But the most surprising cameo was from Rufus Wainwright, who was not even booked to perform at the festival that weekend. Wainwright, 52, came out to perform an elegiac rendition of Bob Dylan’s “Not Dark Yet” after trading verses with Antonoff on the Bleachers song “45.” It was unexpected, but by the time Wainwright took the second verse about “praying at the Nineties” and belted the chorus, he had made the 2020 song his own.  —Jonathan Bernstein

This year, Gracie Abrams leveled up to the mainstage at Lollapalooza after first playing the festival in 2022. Back then, on a smaller stage and at an earlier time, Abrams performed a cover of Robyn’s 2010 hit “Dancing On My Own.” Abrams invited the Swedish pop queen herself to sing the track this year, describing it as “my favorite song of all time, ultimately the best song ever written.” (We agree, give or take a few.) The two singers delivered a dazzling, symbiotic performance of the song, bringing all the heartsick emotions and spinning around each other as they hit each note. It was one of the highlights of the entire Lollapalooza weekend, and of Abrams’ career. In an Instagram post, Abrams addressed Robyn directly: “You have magic powers and by some miracle you are also generous enough to have shared them with us last night… Thank you for making my favorite music.” —M.G.

Olivia Rodrigo has been a Weezer fan forever, and she has the photos to prove it. On Monday, just after Weezer joined her onstage to play “Buddy Holly” and “Say It Ain’t So” for her headlining set at Lollapalooza, Rodrigo shared a photo of herself as a tiny kid, smiling from ear-to-ear in a Weezer T-shirt, and revealed the band was actually her first concert back then. “thank u to everyone who came out and thank u @weezer for still making me this excited all these years later!!!” she posted in the caption. Weezer, meanwhile, seemed just as delighted by the whole thing, commenting on the post, “Full circle moment and an absolute honor, thank you.” —Julyssa Lopez

“We can just let loose, right?” Sabrina Carpenter told her packed Lollapalooza crowd on the festival’s closing night. “We can just groove.” The superstar found a legendary group that could match her effervescent, perpetually cheery take on pop: Earth, Wind & Fire. Members of the funk-soul outfit, including singer Philip Bailey and his soaring falsetto, proved their Rock & Roll Hall of Fame status, delivering “Let’s Groove” and “September” with the same upbeat ferociousness as when those songs first came out four decades ago. Carpenter chimed in with back-up vocals, but wisely and deferentially ceded the stage to the veterans —Jason Newman