Holding Space is a joint column by Anne T. Donahue and Peter Knegt that “holds space” for something or someone in popular culture.

Peter: I need to make a confession, Anne.

Anne: Talk to me.

Peter: Despite the many, many reasons she has given us not to, I am still rooting so hard for Madonna. And I genuinely could not be more excited for Confessions II, her new album/sequel to 2005’s Confessions on a Dance Floor. Am I OK?

Anne: Peter, I will never tell you who you can and can not champion. (Unless it’s Gwyneth Paltrow. Yikes.) But I need to hear more. Revering the Madonna of old is something I deeply understand. You had a huge part in me embracing 20th-century Madonna! Remember our roundtable about Truth or Dare? She was an artist! An advocate! An outspoken critic of the fascist state that is Toronto! (If you’re under 30, watch this video to get that reference.) Also, her music up to and including Confessions on a Dance Floor is unparalleled. But Madonna post-2005 is a different story. There’s a lot to unpack there. 

Peter: A lot. But before we get to that, here’s the thing: even if so much of what Madonna has done in the past 20 years has been a mess, she’s still here, giving it everything she’s got. Look at the months of promo she’s been doing for this new album. She held her own against Sabrina Carpenter at Coachella! She dangled herself from a giant billboard in Times Square while she performed for thousands of gay guys! She released a (legitimately awesome) 14 minute visual companion to the album that reunited her with Debi Mazar! 

WATCH | Watch Madonna’s Confessions II – The Film:

The fact that Madonna did all this while being nearly 68-years-old is undeniably awe inspiring. And so is so much of the story of how she got here. (Have you listened to Bandsplain’s 6 part, 20 hour podcast miniseries on her? It’s incredible). This is a woman who, for the last 30 years of her career, has been told she’s too old to be doing it anymore — in a way that was unquestionably based in ageism and misogyny. And for the most part, she’s proven them wrong at every turn. But I was a little worried she might have hit a wall simply too high even for her in the leadup to the 2023 Celebration world tour, a retrospective of 40 years of Madonna’s career. When she ended up postponing the tour several months because she had ended up in intensive care with a bacterial infection I just thought, “this is it.” But no! She recovered, completed 81 sold out shows all around the globe — one of which I witnessed, and it was glorious— and once again was, against all odds, on top of the world. That could have been a monumental way to go into retirement. Instead, Madonna decided it was time for a whole new era, or at least a sequel to a previous era: Confessions II. And I am finding myself kind of riveted watching her pull it off, even if a lot of what she’s doing is absolutely ridiculous. Madonna has never been shy to pander to her gay fans, but this promo tour has been next level. Anne, she literally took over Grindr so that when you open the app Madonna is there, telling you you’re gay. Not to mention when she turned up at famed West Hollywood gay bar The Abbey shouting things like “Mother is here to save you” and “don’t let me down, gays!” at the crowd. That’s too much pressure, Madonna! 

As someone who is not being yelled at to not let her down, what do you make of all this, Anne? And how do you feel about this umpteenth resurrection of Madonna in general?

Anne:I promise none of my Madonna hesitancy is due to her age. What is age? Keep going until you’re long dead, that’s how I see it! I will never throw side-eye at someone doing their thing at any age.

And for the record, the Sabrina Carpenter/Madonna Like a Virgin moment needs to be uploaded to streaming services ASAP because I must play it loudly from my car as I convince myself I can sing like Sabrina. Her Times Square moment? My brother in Christ, I couldn’t have done that when I was 20, let alone now, let alone 68. Also, everybody just needs to calm down regarding her aesthetic evolutions and how old she is while executing them. If someone gets work done, they get work done. Not my face, not my concern.

For me, the problem is the cultural appropriation she seems hell-bent on committing to. We saw it during the Ray of Light roll-out (cut to: Nothing Really Matters), She compared ageism to racism, she used photos of Nelson Mandela and Martin Luther King Jr. for her 2015 album roll-out and replaced those figures with images of herself.. I could go on. It’s not good. Which I know might be considered an extension of “pushing the boundaries,” but no. Not these ones. There are other boundaries that need to be pushed. Especially by a white woman. We have influencers romanticizing being a “trad wife,” for heaven’s sake. Madonna circa 1989 would shock the shit out of those people.

My understanding of Madonna and her consistent resurrections has, like her public image, evolved. I grew up Catholic, which means that at school we were taught that “controversial” equaled “bad.” My 13-year-old self judged her hard for the abundance of sexual imagery. But as an adult? Hell yeah, Madonna! She grew up Catholic too, so I get why she called out so many religious ideologies and norms and really rejected the shame being projected onto her. I love the way she embraced new incarnations of herself and the music that accompanied those selves. Reinvention is tried by many and achieved by few. I’m so here to see her channel the Confessions era, but I hope she uses this rollout not to … do whatever she was doing in the 2010s. That really bummed me out.

Madonna in a scene from Confessions II - The Film.Madonna in a scene from Confessions II – The Film. (YouTube)

Peter: OK, so in this era where we quickly forget any problematic thing a celebrity has done 10 minutes after they do it, these are very important reminders for those among us who have been overeager to give Madonna a full pass. She is undeniably the queen of cultural appropriation, and that’s been constant throughout her entire career. Although she does seem to have taken the notes this time around. The only stealing happening from this era seems to be from previous self and the wallets of gay men.

We should also get into the music itself, which also has been a bit of a problem since the post-Confessions era, in that most of it hasn’t been very good. There’s certainly a few exceptions. All four of the albums she’s released in the last 20 years  — Hard Candy, MDNA, Rebel Heart and Madame X — have a song or two that I love, but mostly they’ve lacked cohesion. At times, a lot of the music has felt pretty desperate. Remember when she teamed up with Nicki Minaj and M.I.A. for the bubblegum pop cheerleader anthem Give Me All Your Luvin? Literally everything about that has aged unbelievably poorly. Which makes the choice to now return to her last legitimately great album, Confessions of a Dance Floor, almost feel like Madonna admitting that everything since then has sucked. Does that make sense?

Anne: It does! I really checked out after Confessions which, to me, is a perfect pop album. But I figured she was Madonna so regardless of what I thought about her, I assumed that she’d still be raking in the big bucks and maintaining her fanbase. Which I wasn’t wrong about!

I want to see her release music that reminds anybody who didn’t grow up listening to her that she was crowned the Queen of Pop for a reason. The ‘80s, ‘90s, and the first half of the ‘00s were a marathon of hits. Even Don’t Cry For Me Argentina stood the test of time once it was remixed. (At least in my opinion, as a person who loves both dance music and showtunes.) She was a cultural phenomenon! She really did change the conversation regarding what could and could not be done in mainstream music. If this new album can work as a testament to legacy over novelty, it could introduce her to a Gen Z audience who will be inspired to acquaint themselves with singles other than Vogue.

What do you think? Your relationship to Madge is a lot different than mine. I like her music, but your love runs deep. Tell me more about that and whether it’s even exciting to find out about new music, or if it’s just stressful since you don’t want to be let down. I mean, everybody was relatively psyched about Harry Styles and Drake this spring and, well, they weren’t The Immaculate Collection, that’s all I’m going to say.

WATCH | Madonna’s “Like a Prayer”:

Peter: Seeing her release music that reminds people who are unaware why she was crowned the Queen of Pop is, to me, the ultimate thing Madonna could do at this point. My love for her is complicated, but it certainly does run deep. Like a Prayer was my all time favourite song from age 7, and will be until whenever I die. And I want Gen Z and Gen Alpha and Gen Beta and Gen whatever comes after that to all be well aware that once upon a time there was a woman named Madonna Louise Ciccone and the collections she released were indeed immaculate. 

Do I think that’s going to happen with Confessions II? Probably not! The fact that she reteamed with the OG Confessions producer Stuart Price felt very promising, and I’m very into some of what I’ve heard so far (I Feel So Free, Danceteria). But I’ve also been less impressed with others, including the underwhelming, nonsensical Sabrina Carpenter duet — if you can even call it that — Bring Your Love. It seems to me that she’s mostly playing hard to her most devoted fanbase, gays over 40. Which doesn’t feel desperate to me, it just feels natural.

Unfortunately, I do think what it’s really going to take to bring Madonna to the younger masses is something she has not quite been able to pull off: a biopic movie. We’re well aware she’s been trying to make one herself for ages, and she just told Interview magazine these plans are now indefinitely on hold because she had a falling out with Universal Pictures. I can’t quite land on whether I’m relieved by this or not. On the one hand, I generally despise music biopics for watering down the truth into a whitewashed oblivion. On the other, I am obviously deeply curious to see what a Madonna biopic directed by Madonna would look like. It could be the most glorious mess we’ve ever seen on screen, Anne.

Anne: The fact that Julia Garner was going to be playing Madonna, too! It was lining up to be a biopic that would actually be compelling and interesting and, dare I say, good. But alas, nothing gold shall stay.

That said, I think a documentary in the style of with Truth or Dare would reel in a younger audience. Or a memoir. And not a “dictated to a writer” memoir, one that she actually writes that embodies the best parts of Madonna the performer: honest, strong, bold, extremely human. I feel the same way about Bring Your Love as you do, but because I think it lacks Madonna’s full Madonnaness. I Feel So Free certainly nods to it, but when I listen to Rescue Me or Erotica there’s something so present in her voice. Like immediately you know why those songs transfixed the masses, for better or for worse.

I just hope Confessions II is the former.

Peter: Shall we have, like, a prayer for that?

Anne: Only if you call my name.