The comments came as the singer prepares to release Confessions II, her follow-up to 2005’s Confessions On A Dance Floor, after spending the past year in the studio with longtime collaborator Stuart Price.
Madonna had previously been linked with Glastonbury in 2024 after launching her Celebration Tour in London, where festival organizer Emily Eavis was spotted in the audience, but she instead returned to recording.
Sources now tell us she could headline the Somerset festival in 2027.
But one music industry insider said Madonna had little interest in accepting a heritage booking and being placed into the Legends slot, which falls on the final evening of the festival as the sun starts to go down, as she views it as a “grandmother or grandad’s gig.”
The source added: “Madonna has enormous respect for Glastonbury, but she has never viewed herself as a nostalgia act. The Legends Slot celebrates extraordinary careers, yet she believes it has become associated with artists revisiting past glories, like Dolly Parton.
“In her mind, she is still making new music, pushing creative boundaries and competing with today’s biggest stars, so she would rather headline the festival than be presented as a legacy performer.”
Another insider close to festival planning said: “Madonna doesn’t want audiences thinking she has reached the stage where she is being honored for what she achieved decades ago. Madonna has built her career on reinvention, and she still sees herself as a contemporary artist. Accepting the Legends Slot would send the wrong message from her perspective – she wants the Saturday night headline spot.”

