I Am Cringe, But I Am Free

From the Rock & Roll Tarot by Massimo Galloni

I'm listening to Madonna's later albums and facing my fears, I recently texted a friend.

This friend and I have been listening to a special four-part series on (my favorite music podcast) Bandsplain, hosted by the incredible Yasi Salek, about Madonna.

Each episode is 1,000 hours long and honestly I could listen to more. They have made me understand even more clearly Madonna's insane contribution to American pop music and culture, and inspired the aforementioned journey into her "later" albums. But why Madonna? Who cares? She is old. She is plastic. She won't shut up. She jumped the shark a long time ago.

Obvy not everyone feels this way (and for the record I don't feel this way); she has jillions of superfans, many of them the gay men she has celebrated since her early days as a dancer in NYC until now, where, yes, she continues to exist, broadcasting beats from her goddess-plane in the body of a 67-year-old female athlete (soon to be 68). But I feel like I am swimming in a sea of Madonna hate more than Madonna celebration, (shamefully) causing me to be somewhat reluctant in my fandom.

More on that in a sec, but first— the "later" albums.

For me, those are everything after Music, released in 2000, at which point she'd been putting out music for nearly twenty years. I played the shit out of that CD on my stereo in my glorified closet of a bedroom in a mobile home in a trailer park in Las Cruces, New Mexico, where I was doing an AmeriCorps year.

I was in my early twenties, and being in my forties, as Madonna was in that video, and as I am now—felt as otherworldly as the New Mexico sky. At 22 I would have considered anyone in their forties old. But I didn't consider Madonna to be old in the video for the "Music" single (a song I love but not as much as I love "Don't Tell Me"– the cowboys dancing!!).

In the "Music" video, she wore a white pimp suit and a cowboy hat and was partying in a limo with Ali G, legendary backup singer Niki Haris and bestie Debi Mazar. Her age didn't matter to me. It didn't matter to me because it didn't appear to matter to her. Madonna didn't act like anything had changed. She didn't act "middle-aged". Nor did she act pregnant, which she was during the filming of that video.

Madonna would never succumb to the idea of herself as anything less capable, less mobile, less fit, less hot, less ready to work her ass off, less ready to party than she was in her twenties. Even then her age didn't matter to her. Well, I'm sure it mattered to her only because it mattered to everyone else. She had to absorb everyone being like "uh-oh, Madonna's forty, how is she still alive?"

But I don't remember getting into that album with any of my friends. Did I just need better friends??

Even as a fan of Ray of Light, the album before Music, I felt displaced in my peer group. "Turn this off," my friend Jenny said when I was playing the song "Frozen," in her janky 1994 Toyota Corolla. "Madonna has nothing to say." Because I am of a docile nature, and I hadn't really thought that hard about the instinct to defend Madonna I had even back then, I didn't stand up for her. I turned off "Frozen" and accepted Jenny's opinion. Because I was a little pervious at the time, I think I let it unconsciously guide me.

Hence, after Music, I perked up for the singles "Beautiful Stranger" and "Hung Up", but I had lost interest in Madonna. I had moved on. I think I was dismissive of her throughout the aughts and early 2010s. Even though so many Madonna songs are dear to my heart, I had adopted the stance of the heterosexual white majority, and of the staunch fans of her earlier work: why listen to Madonna now? She could never be as good. Because she was getting so old. Shouldn't she be too tired?

Back to those so-called later albums. What was so challenging, for me, about listening to them? What was I afraid of, anyway, in listening to her later work, the dance music made by a woman in her late forties, fifties, and sixties? I am a feminist. But am I ageist? Was I terrified the music would be bad? Afraid it would be good? Afraid that she would be making a fool of herself, which is somehow worse when you're middle-aged and older, especially if you're a woman?

Yes. All of those things!

Those fears are exactly what holds me back not from making art of my own, but from sharing it with other people. Even putting this miniscule bit of writing on the internet steeps me in dread. I'm afraid it will be bad, or good, or that I will be making a fool of myself, because I can't afford to make a fool of myself at age 47, almost 48, almost 50 years old!! So dumb. I don't want to lurk in the shadows of fear. And I shan't. Madonna certainly does not!!

Listening to those "later" albums—an entire catalog of music from an artist I presumed to know pretty well–has been an almost ecstatic pleasure for me. This list includes American Life (2003), Confessions on a Dance Floor (2005), Hard Candy (2008), MDNA (2012), Rebel Heart (2015), and Madame X (2019).

Because truly, many of these "new-to-me songs" I fucking love. And there's a sense of relief that, quite undramatically, the songs are subjectively good, bad, "eh,"—and sometimes very weird—just like anyone else's music. Just like Bob Dylan's music, which often really sucks.

I get the cringe about old Madonna, especially when the music she made, and the personas she presented as a young person, were so good, and she was so gorgeous, and her way of being a pop star was so earthshaking for my generation.

But Madonna will Madonna. She has continued to evolve, continued to ignore her age (except for getting plastic surgery, and I'm sure she has to rest more), and continued to make new works, like any worthy artist does. I just watched her short film for Confessions II (out next months) in which she is still extolling the powers of the dance floor and writhing her body amongst other bodies (and weirdly, Benedict Cumberbatch). Green lasers shoot from her crotch. She is still presenting herself as a sexual being, and not just a sexual being but a bit of a perv. Amen. We need more mature female pervs. Viva la randy crones.

Now, at the age of 47–the age Madonna was in the video for "Hung Up" in which she looks stunning, like the world's most intimidating aerobics instructor–I stand up for Madonna. (Fuck you, Jenny!) I am far less pervious to other people's negativity. I defend Madonna and even listen to her as she ages, and as I age. I need her to keep being Madonna because, I have discovered, I like basking in the disco ball light of her very well-earned wisdom, always twenty years ahead of me, always proclaiming her most effective refrain: let's dance.

I need her to be Madonna no matter her age, because I need her to keep showing me how not to care what people think. Because she's like a deity, an archetype, the High Priestess on the tarot card. I want her to be 95 and making an album with someone who, right now, in the year 2026, hasn't even been born yet, and I want her to be sleeping with them, too. When Madonna stops acting that way, it will be the first sign of the Apocalypse.

It's joyfully absurd to be almost 48 and going through perimenopausal puberty and still anticipating new Madonna music. Confessions II comes out next month. (!!) Is it Cringe? Maybe. But, as my hero Yasi Salek says, "I am cringe, but I am free."