Madonna’s Confessions II – The Film has generated exactly the response she will have hoped for. Sixteen celebrity cameos, including Benedict Cumberbatch voguing in a bathroom, Kate Moss in a nightclub restroom and Sabrina Carpenter on a dancefloor, have had us agog, debating who we are most thrilled to see sharing a frame.
But if you look past the famous faces and beyond the marketing genius, something more interesting is happening. The reason Madonna chose these people to appear reveals more about what is of value right now, more than any trend report or cultural forecast could. This is a film about what really matters by someone who has spent 40 years paying close attention to some of the biggest questions about how we live now.
Here is what the cameos are really telling us.
Long friendship is the ultimate flex
For younger viewers, Debi Mazar is perhaps best known from Younger or Entourage. But the reason she is at the heart and centre of this film has nothing to do with her current profile. Madonna wrote the song “Danceteria” about the legendary Manhattan nightclub where she first arrived in New York as a broke, ambitious 20-year-old in the late 1970s, and Mazar was part of that same scene.
They have been friends for close to 45 years and this is not a one-time deal; every Madonna superfan knows she has brought her distinctive New York energy to several of Madonna’s iconic music videos, “Papa Don't Preach”, “True Blue”, “Justify My Love”, “Deeper and Deeper”, and “Music”. They have shared the highs and lows that only 40 years of being in each other’s lives can bring. Here, Madonna is telling us that you’ll make new friends throughout your life, but you can never make old friends. Bask in their orbit, make them the centre of your universe.
Being older is cool, actually, it makes you the most interesting person in the room
The moment in the film where Madonna mentions cocaine and the camera cuts immediately to Moss doing a hair flip in a nightclub bathroom mirror generated the first viral clip of the film’s rollout and only Madonna could be quite so on the nose (pun intended).
It works because, to land, it requires knowledge of a cultural backstory. You have to know who Kate Moss is, what she represents, and what the joke is. It's more obvious than a Taylor Swift easter egg, but it’s a cameo that rewards the initiated. But there is something larger underneath it. Madonna and Moss are both women who pop culture has repeatedly tried to retire, and both have refused. Kate’s cameo is an empowering moment for Madonna’s Gen X audience, women who grew up with both icons and understand instinctively that maturity isn't something to survive culturally, but something to celebrate. The most interesting person in the room is usually the one with the longest history. And resilience depends on not taking yourself too seriously.
It’s our duty to pass on the baton
Madonna admitted at the Tribeca premiere that she almost did not ask her 29-year-old daughter Lourdes to appear in the film, because Lourdes routinely declines anything that connects her to her mother’s world. So, her appearance is telling. The two have also co-written a song together for the album called “The Test”. That Lourdes gets the last word in a film her mother has poured her creative life into is telling. Those closing words? “Cut, b*tch.”
Loyalty is everything
Julia Garner. This is the casting choice that carries the most complex emotional weight because Garner was announced as the actress set to portray Madonna in her long-gestating biopic, a project that has been developed, shelved by Universal, and picked back up repeatedly over the years. The biopic may or may not happen. But Madonna has put Garner in the film she has full control over, on her own terms, in her own visual language (Blonde Ambition era), bringing someone the industry casually left waiting, is an act of loyalty that says the relationship matters more than the project's status on a studio slate.
Madonna is telling us that you’ll make new friends throughout your life, but you can never make old friends
See too Richard E Grant, who starred in Madonna’s directorial debut, the 2008 indie comedy-drama Filth and Wisdom, playing Professor Flynn, a blind and frustrated poet. Grant later revealed that Madonna personally convinced him to take the role by playfully flirting with him over the phone, and that he is now in her most ambitious visual project nearly two decades later, which shows she does not forget the people who trusted her.
Look forward, don’t just look back
Sabrina Carpenter is one of the biggest pop stars of the current moment, and her presence here is Madonna saying she is paying attention to now, not just to then. But it also says something about Carpenter, that she wants the co-sign; she recognises that there is no now without then and she is happy to stand next to pop's original architect.
Stop being a try-hard; we’re all no-brow now
A prestigious British actor voguing in a bathroom has no obvious cultural logic, but including Benedict Cumberbatch is a deliberate provocation and says high culture and club culture are the same culture, and always have been. It is also saying it is cool to include someone who has no business being there and make it work through sheer conviction and that the cast list doesn't need to make sense, that would make you a try-hard.
Cumberbatch once revealed on The Graham Norton Show that he had auditioned for a project Madonna was directing. She arrived late, breezy and unhurried, holding a clipboard. She looked it over, held it up to her face, and deadpanned: "Benedict Cumberbatch... is that really your name?" He confirmed it was and he did not get the part. That he is now in her film has the quality of a very long punchline. The people she finds interesting are the people who can take a joke and still show up.
Madonna’s heart will always be in the underground
Honey Dijon, Shygirl and Arca. These three names will mean everything to one audience and relatively little to another, and that gap is precisely the point. Honey Dijon is one of the most respected DJs and producers working in house and club music today, a Chicago-born figure whose career traces a direct line from the underground ballroom scene to the global festival circuit.
Shygirl is the British artist who has spent the past several years making some of the most genuinely strange and thrillingly uncompromising music in the UK, sitting at the intersection of club, rap, and avant-garde pop. Arca is the Venezuelan-born experimental producer and artist whose work exists almost entirely outside of any commercial framework. Madonna may be mainstream, but the underground has always been her home.
When worlds collide, exciting things happen
Cole Palmer is one of the most talented and talked-about footballers in England, while João Pedro is a Brazilian striker whose career has taken him from Watford to Brighton and now to Chelsea, where he is a teammate of Palmer’s. Neither has an obvious connection to the world of pop music or fashion but the dancefloor she is describing is one where the barriers between worlds have come down entirely, and the mix of people matters. There is no hierarchy here. There is no VIP list. There is just the room, and who is in it. To be an influencer who thinks you’re better than anyone else is just embarrassing.
Social media is so very over
Madonna has spoken: Confessions II is designed to do what dance music has always done at its best: get people into a room together and make them feel less alone. In 2026, with loneliness classified as a public health crisis, human connection through physical presence and shared experience is what really matters. To be an influencer who thinks you’re better than anyone else is just embarrassing. Being in a room with other bodies moving to the same beat, enjoying the moment, not posting the moment, is where we all need to be.
Dan Wakeford is the former editor-in-chief of ‘People’ magazine and ‘Us Weekly’, and founder of Celebrity Intelligence
