Madonna shared the spotlight with a familiar face from her past as she reunited with former boyfriend Tony Ward during her opening performance at the 2026 MTV Video Music Awards.
The singer, 68, appeared alongside the model and actor at the ceremony in Los Angeles on September 27, some 35 years after their relationship ended.
Tony featured in a bathroom sequence during the performance, a reunion that carried a particular connection to Madonna’s music career: he famously appeared in her provocative “Justify My Love” video in 1990.
© Penske Media via Getty ImagesThe appearance was part of an elaborate opening number featuring Sabrina Carpenter, Charli xcx and several other famous guests, marking Madonna’s first VMAs performance since 2003.
Madonna’s reunion with Tony Ward
Madonna and Tony dated between 1990 and 1991. Their professional relationship produced one of the most talked-about videos of her career. MTV declined to air “Justify My Love” because of its sexually explicit content, making Tony’s appearance alongside her at the network’s awards show a notable return.
The couple’s creative connection continued after their romance ended, with Tony also appearing in Madonna’s 1992 photography book, Sex.
© Getty ImagesDecades later, their latest collaboration brought that shared history into a performance celebrating a new chapter in her music.
A performance packed with famous faces
Madonna opened with “Bring Your Love”, joined by collaborator Sabrina Carpenter, before Charli xcx appeared for “Danceteria Afterhours”.
© CBS via Getty ImagesThe guest list extended beyond her fellow singers. Actress and longtime friend Debi Mazar, Julia Garner, Seth Rogen and musician Sombr also featured, with the performance recreating scenes from her Confessions II film.
Sabrina embraced the theatrical styling in a white shirt, sequinned black briefs, braces and a beret.
The staging moved through club and bathroom settings, weaving the celebrity appearances into the world of Madonna’s latest project.
Madonna’s history-making VMAs appearances
The performance added another chapter to Madonna’s long association with the awards.
At the inaugural ceremony in 1984, she performed “Like a Virgin” in a wedding dress. Her elaborate rendition of “Vogue” followed in 1990, while her 2003 performance with Britney Spears and Christina Aguilera became another defining moment in the show’s history.
© WireImageAlthough she has appeared at the ceremony since then, this year’s opening number was her first VMAs performance in 23 years. The distinction made the evening a musical comeback to the awards stage, as well as an opportunity to reunite with past collaborators.
Seven awards for the Queen of Pop
Madonna’s evening also brought a substantial haul of trophies. She won seven awards, including Artist of the Year, Best Album for Confessions II and Best Collaboration for “Bring Your Love” with Sabrina.
Her Confessions II film collected honours for Best Dance, Best Long Form Video, Best Choreography and Best Cinematography, completing a night that celebrated both her new music and the visual storytelling that has defined her career.
