No one does the Video Music Awards quite like the queen of pop. Since 1984, Madonna has delivered so many memorable moments from one of music’s biggest nights, and on Sunday, Sept. 27, she made history once again with a live set that packed in plenty of celebrity cameos and Easter eggs from her four-decade-long career. Opening the show, Madonna’s 2026 MTV VMAs performance was truly a return to form as well as a celebration of her past, present, and future artistry.
This year, the pop culture icon released Confessions II to both fan and critical acclaim, and Sunday’s awards show was a reflection of that. With 13 nominations — the most of the night — the album solidified Madonna’s status as one of the foremost names in dance music, and her opening performance proved this fact even further. Set in a club bathroom, the 8-minute-long set kicked off with “Bring Your Love” alongside Sabrina Carpenter, who was clad in glittery short shorts, suspenders, and a beret, while the 68-year old star sported a belted satin coat over a wine-colored bodysuit, knee-high boots, and her ever-present fingerless gloves.
As the performance unfolded, the icon’s other Confessions collaborator, Charli XCX, joined in on the fun, emerging from a bathroom stall wearing a custom Dsquared2 look, cigarette in hand. The two launched into “Danceteria Afterhours” as Charli moved across the stage in her micro-mini dress and fishnets — a fitting ode to Madonna.
But of course the references didn’t stop there. As the set continued, more and more stars appeared. Of course long-time BFF Debi Mazar was present, as was Julia Garner (who was once rumored to play the pop star in a now defunct biopic), cone bra and all. Additionally, Gabbriette, Sombr, and a leather-clad Seth Rogen made notable cameos with nods to Madonna’s past performances and videos sprinkled throughout.
CBS Photo Archive/CBS/Getty Images
The fact that so many celebs turned up for Madonna comes as no surprise, considering that her last VMAs performance in 2003 famously ended in kisses with fellow pop stars Britney Spears and Christina Aguilera as she seemingly passed the torch. But over two decades later, the singer proved she’s still a force to be reckoned with in the scene, taking home seven awards including Album of the Year and Best Collaboration.
CBS Photo Archive/CBS/Getty Images
Changing out of her performance look, Madonna accepted her awards in another on-brand outfit, a pair of black short shorts with a matching corset and lace gloves. And as she mingled with fellow attendees like Taylor Swift, she layered the look with a leather biker jacket — a quintessentially VMAs piece. Serious icon behavior.
(Stay Up To Date)
Become A Style Insider
Join The Zoe Report’s exclusive email list for the latest trends, shopping guides, celebrity style, and more.
