Madonna waited 23 years to perform at the MTV Video Music Awards again. When she finally returned Sunday night, she brought Sabrina Carpenter and Charli xcx with her, then spent the rest of the ceremony collecting awards.
The 68-year-old opened the Sept. 27 show at the Peacock Theater in Los Angeles with her first live VMAs performance since the 2003 opener featuring Britney Spears, Christina Aguilera and Missy Elliott.
PEOPLE described a performance that moved from a fog-filled opening and spoken-word introduction into “Bring Your Love” with Carpenter and “Danceteria Afterhours” with Charli.
The comeback was only the beginning of Madonna’s night. MTV’s official results show her finishing with seven wins, more than any other artist at the ceremony, including Artist of the Year and Best Collaboration with Carpenter for “Bring Your Love.”
The Performance Started With Sabrina Carpenter at the Piano
View this post on Instagram
Madonna’s return began with a spoken-word introduction from “One Step Away” before Carpenter appeared at the piano for “Bring Your Love.” Madonna initially sat above the instrument while Carpenter played below her, then the production expanded into a much larger dance set as the song progressed.
Carpenter wore a white button-down, glittering black shorts, suspenders and a beret for the duet, a look that nodded toward Madonna’s early-1980s style. Vogue noted that Madonna paired a satin black mini trench with a pink bodysuit, corset and thigh-high boots, while PEOPLE identified the lace-up Saint Laurent boots as a piece from her original Confessions on a Dance Floor era.
Her Return Came 23 Years After the Britney Spears and Christina Aguilera Kiss
MTV had announced before the ceremony that this would be Madonna’s first live VMAs performance in 23 years. Her previous one came during the 2003 opening medley with Britney Spears, Christina Aguilera and Missy Elliott, remembered especially for Madonna’s onstage kisses with Spears and Aguilera.
The 2026 performance approached the generational handoff differently. Carpenter and Charli appeared as current collaborators rather than younger singers revisiting Madonna’s catalog, with both “Bring Your Love” and “Danceteria Afterhours” tied to the Confessions II era. Variety described the opener as a two-song showcase for Madonna’s current material instead of conventional career retrospective.
Her VMAs history stretches much further back than 2003. PEOPLE noted that Madonna performed “Like a Virgin” at the inaugural ceremony in 1984, creating one of the earliest defining images in the show’s history, and became the first solo female recipient of the Video Vanguard Award two years later.
Artist of the Year Brought Madonna Back to Her 1984 VMAs Debut
Madonna returned to that first VMAs appearance when she accepted Artist of the Year later in the evening. PEOPLE reported that she recalled losing a stiletto during “Like a Virgin,” diving to the floor to make the mishap look intentional and accidentally exposing part of herself in the process.
Madonna said she went backstage feeling proud of the performance only to be told that her “career was over.” More than four decades later, she used that memory to contrast the reaction to her early provocations with where her career had ultimately taken her.
Rolling Stone noted that the second half of her speech focused on the present. Madonna said she had spent the previous year and a half finding and believing in herself while making the music she wanted to make, then encouraged the audience to do the same in their own lives.
Madonna Ended the Night With Seven Wins
View this post on Instagram
Madonna’s final tally went well beyond Artist of the Year and Best Collaboration. MTV’s official winners list shows Confessions II winning Best Album, while Confessions II – The Film took Best Dance, Best Cinematography, Best Choreography and Best Long Form Video.
Combined with Artist of the Year and the Carpenter collaboration, that brought Madonna to seven awards for the night. AwardsWatch noted that seven represented the biggest single-night VMA haul of Madonna’s career and her first wins at the ceremony since 1999.