Following her surprise Coachella Weekend 2 appearance with Sabrina Carpenter on April 17—where they dueted 'Vogue' and 'Like a Prayer' and debuted 'I Feel So Free' live—Madonna's manager Guy Oseary called it a full-circle celebration 20 years after her festival debut. He shared Instagram praise and backstory from their first encounter, with Carpenter responding enthusiastically.
In a performance detailed in prior coverage of the 'I Feel So Free' launch, Madonna joined Sabrina Carpenter onstage at Coachella's main stage, joking, 'The thrilling thing I need to point out to everybody right now is this probably is the first time I’ve ever performed with someone who’s shorter than me,' to crowd cheers.
The next day, April 18, Oseary posted on Instagram: '20 years since @madonna first performance at @coachella, a beautiful full-circle celebration.' Sharing video clips, he thanked Carpenter and her team, recalling their initial meeting at the SNL 50 party in February 2025, where Carpenter sang 'Like a Virgin' impromptu and voiced her Madonna fandom.
Carpenter replied to Oseary's post with three pink revolving heart emojis. She later shared her own photo gallery, captioning: 'Coachella weekend 2 might take the damn cake.' Profusely thanking Madonna, she wrote: 'Madonna …..I’ve got something i wanna talk about! thank you for coming out, bringing your love, and gracing the audience with everything you are + astrology knowledge + the greatest songs of all time. Last night was straight out of a dream.'
'I Feel So Free,' a house track about dancing's 'safety in numbers,' premiered on iHeartRadio’s Pride station April 17 and was officially released April 19. It's from Confessions II, produced with Stuart Price (of 2005's Confessions on a Dance Floor), due June 3—Madonna's first new album since 2019's Madame X.
