Weekend 10: Madonna, Myself

On the occasion of her 66th birthday, please enjoy my personal Top 10 favorite songs from the original pop icon, Our Lady Madonna.

Weekend 10: Madonna, Myself
Judging/ogling a sweaty, dirty male proletariat while wearing custom Jean-Paul Gaultier? All in a day's work, babes.

Welcome to The Enthusiast, the newsletter that is about to be renamed very soon! Yes, hi, hello, I'm here, I missed you, I've missed writing this, and I hope you missed reading it, even just a little bit? And if you're new, welcome! You've come across this newsletter (and by extension, me) at a bit of a strange time, but rest assured there's more to come and then some as this little experiment comes into its second year(!!).

When I finally do get my shit together, remember to take my fiber and probiotic daily, consistently practice yoga every morning, and stop revenge-bedtime procrastinating, it's about to be OVER for y'all. Until then, have some Madonna!


Okay, so, I was not allowed to watch MTV as a kid, which blows a LOT of my fellow Millennials’ minds, given our youth was the delirious apex of the music video in all its ridiculous, groundbreaking glory. But somehow, some way, many of Madonna’s early videos permeated my consciousness, because I truly don’t recall the first time I saw one or even when heard my first Madonna song–she just was always there, presiding over pop since the day I was born ("Lucky Star" was peaking at #8 on the Billboard Hot 100 that week). She released her self-titled debut in 1983, followed by Like a Virgin in ‘84, so there has never been a time while I have drawn breath in this world that Madonna wasn’t in it.

Reader, I was not prepared.

I tried to pretend I wasn’t losing my shit when I got nosebleed tickets to see her in her hometown of Detroit (in January, no less). I tried not to listen to every single album and all my faves on repeat in the weeks leading up to the show (I failed lol). I didn’t want to dress up for the show because it was -1 in Detroit as we walked to the arena in several inches of ice-crusted snow, but I had to slap my own hand away from giving myself a faux eyeliner beauty mark. And I didn’t want to find myself sobbing in overwhelming exhilaration when she finally rose up from the floor in dozens of yards of windblown chiffon and a crown of stars to open with “Nothing Really Matters,” but I absolutely and unapologetically did. 

The ensuing 2+ hours were nothing short of miraculous: a journey through hit after hit, reinvention after reinvention, a true celebration of one of the most influential and iconic Americans to have ever dropped her last name and become a self-made icon in the purest sense of the word (literally from the Greek “image,” and later a venerated representation of a sacred entity—form and meaning bonded together in a single visual). No shade to my Swifties, but Madonna had already carved out at least two or three eras by the time Tay-tay was out of diapers. 

Promoting the yee-haw agenda since 2000.

Truly, it was the concert of a lifetime for me: 40 years of my own life reflected back at me through the culture Madonna herself defined, so much so that I went again by myself in Atlanta three months later, this time with a floor seat to make up for the viciously narrow Detroit seats that ended up severely bruising me every time I tried to wedge myself back into them. It was worth every penny and maybe even some of the Ticketmaster gouging as well to go again and feel it once more, to give myself the gift of that experience, except closer and with a sense of physical freedom there on the floor where I wasn't terrified of falling to my death or maiming my body between armrests.

All this to say: here are my personal top ten favorite Madonna tracks – on the occasion of her 66th birthday yesterday, having recently finished her tour in front of 1.6 MILLION people in Rio, a year after she survived a near-fatal bacterial infection, and weeks after several dumbasses dropped pointless lawsuits against her for not starting on time and for being too warm at her show (LOL have you even been to a concert, ever?) and bringing an 11 year-old to a concert you KNEW damn well wasn't going to be PG-13, Justin – across all her eras, genres, ages, moods, and beyond.

#10 - "Bitch, I'm Madonna" Rebel Heart, 2015

Madge snagged more celeb cameos for this video than all three seasons of The Bear combined.

I confess I have yet to listen to anything on Madonna's most recent album, 2019's Madame X, but Rebel Heart had some excellent bangers, including this bratty, self-aware club track featuring Nicki Minaj (and every mid-2010's music-adjacent star you can name in the video). It’s a big, obnoxious, and extremely catchy song, right down to the bizarre, jagged beat drop near the end. Her vocals have a fun, punky edge, especially where she straight up screams “Who do you think you are?!” before the chorus, a tongue-in-cheek callback to a time when she probably had to answer that very question over and over from so many people who ended up mattering very little in the long term. Co-written with Minaj and the late SOPHIE and co-produced with Diplo, it’s a bop blessed with that very distinct Madonna attitude. She closed the show with this one, amid a sea of dancers in dozens of different versions of herself—unabashedly self-mythologizing and leaning into high camp at its finest.

#9 - "Into the Groove" Who's That Girl: Desperately Seeking Susan OST, 1985

I've always wanted to try this, but wouldn't it just make you hotter and therefore more sweaty?!

Despite MTV being verboten, VH1 was somehow slightly more acceptable, and thus I absorbed a ton of belated 80’s music video classics thanks to my BFF Pop-Up Video. I absorbed so much random knowledge from their little blurbs and annotations AND got caught up on what I was missing over there on the forbidden Music Television. Maybe it was because VH1 also had Behind the Music and could ostensibly be considered “educational” until it devolved in celebrity-dating dreck in the Aughts?

Anyway, “Into the Groove” is one of my favorite mid-eighties songs in general, full stop. It feels a little raw and unformed, the early dance-pop beat almost stark, and her charisma shines through with her definitive “And you can dance!” line at the very start, followed coyly by “For inspiration…” How can you resist, especially when she reminds you just before the main vocal kicks in: “I’m waitinnnnng…!” It was her first #1 hit and remains her best-selling single of all time for obvious reasons.

#8 - "Turn Up the Radio" MDNA, 2012

Not one Madonna Louise Ciccone partying with the girls out in a chauffeured convertible on the crowded streets of mother Italia!

I will be the first to admit that it's been mostly meh for Madonna's albums after Confessions on a Dance Floor, but I think this fun little track from MDNA didn't get the attention it deserves. Madge likes to get deep and moody these days, but she also still knows how to turn a party track. “Turn Up the Radio” combines the sweet throwback vibes of “Cherish” with the big beat drops of “Ray of Light” for a thoroughly modern dance-party jam. The lyrics are a bit weird and random, but we don't rely on Our Madge for poetics, do we?

#7 - "Dress You Up" Like a Virgin (1984)

There is only a live video for this song, and it is not nearly as impactful as these turn-of-the-millennium GAP ads. Everybody in VESTS, though?!

Where my late-90’s/early-Aughts GAP fans/future employees at? I was never for anyone in khakis or weird sweater-vests, but you can’t deny that indelible cultural impact those louche singing models on a stark white background had on our Millennial psyches. “Dress You Up” is not on The Immaculate Collection, Madonna’s first and truly definitive greatest hits collection, so I was less aware of it until it was on a non-stop loop on my GAP store’s soundtrack in 2001-2002, but it quickly became one of my faves. It’s fun, flirty, and focused on fashion, which has always been a hallmark of Our Lady Madge’s best jams. Featuring guitar licks and co-production from Chic’s Nile Rogers, it’s a great transitional sound from her early disco-esque dance floor grooves to a more full-throated pop approach.

#6 - "Secret" Bedtime Stories (1994)

In her "Jean Harlow Blonde in Lingerie But With Boobs and a Nose Ringand dark nail polish" era here.

I’m pretty sure I only had a vague notion of what “sexy” meant when I first heard this sultry jam on the radio in the 4th grade, but “Secret” quickly became a defining mid-90’s Madonna joint for me, the best among several extremely underrated tracks on the also extremely underrated Bedtime Stories. Sandwiched as it was between the iconic Erotica and the ground-breaking Ray of Light, Bedtime Stories doesn’t get near enough respect for its Dallas Austin & Babyface-helmed R&B vibes (“Human Nature,” “Bedtime Story,” TAKE A BOW!!). However, when the beat drops on that acoustic rhythm guitar at the beginning of “Secret,” you somehow already know what “sexy” means, and spoiler alert: it’s this, and that's all you really need to know. 

#5 - "Hung Up" Confessions on a Dancefloor, 2005

From sampling ABBA to literally naming John Travolta as one of her inspirations for it, there's a lot of concept for such a relatively minimalist video (I love it).

It’s difficult to pick a single best track from Confessions on a Dancefloor, because in my view, it’s one of Madonna’s only albums that’s a true straight listen, and not just because the tracks are mixed into a seamless flow. Not every song stands out, as a result, but “Hung Up” is by far the ear-wormiest and the perfect introduction to kick off a tight hour-long dance party. With all due respect to ABBA (from whom Madonna received a personal blessing to use the sample), every time some rude individual decides to play "Gimme Gimme Gimme (A Man After Midnight)," I am tricked into believing I'm about to hear one of my favorite Madonna tracks and can't help but be sorely disappointed when those sweet, sad Swedes start singing instead. Can we just retire that jersey and let Madonna's reimagining take over, y/y?

4 - "Vogue" I'm Breathless: Songs from Dick Tracy, 1990

Everything about this video is perfect; however, I do find it HILARIOUS that one of her most iconic smash hits came from the soundtrack of a truly godawful summer popcorn movie.

Depending on your age/generation, this is one of a few defining Madonna songs/videos; “Like a Virgin” is emblematic of the early 80’s, “Material Girl” squarely planted in the mid-80’s, and “Vogue” seamlessly transitioning from the excess of the late 80’s and to the severe, sleek glamour of the early 90’s. “Vogue” Madonna is truly my Madonna, platinum blonde and red lipped, gyrating athletically and unashamedly, trussed up in Gaultier pinstripes and conical brassieres. Try not to snap along to those razor-sharp echoing finger snaps in the opening, before the throbbing throwback bass kicks in and the quintessential 90’s dance-pop beat drops to remind you that the dance floor is indeed the place where you can get away.

"Vogue" was also the first of many future appropriations Madonna would help herself to alongside vinyasa yoga, Kabbalah, and being British. I am pleased that the actual, queer history of voguing and ball culture in general is being featured and embraced—it was a highlight of her show, too, starring her small army of amazingly talented dancers paying homage to the art's inherent queerness. She brought David Harbor, of all people, onstage to be on the judging panel in Atlanta, and he high-fived me as he exited the stage (legit that’s how close my seat was). He looked mostly pleasantly and sweatily confused, but he was clearly just as exhilarated as the rest of us.

#3 - "Die Another Day" American Life, 2002

I could write a whole thesis on the cinematic influences on Madonna's music and vice versa, but I'm sure a dozen other nerds already have. Also, content warning: I forgot that she's literally being tortured at several points in this video.

If you told me that Madge’s contribution to the James Bond theme canon would eventually become one of my all-time favorites of any song by any artist, I would have laughed until I actually heard this sinister, esoteric Mirwais-produced banger and it seared itself into my subconscious with reckless abandon. "Die Another Day" is an objectively weird, dense song that only us true freaks really know or care about (I recently sang it in a private karaoke room and my friends were all mildly confused but supportive nonetheless). Only recently did I start paying closer attention to the lyrics; they hit different when you’re pushing 40, and it feels more like a song of survival and resilience than a throwaway theme for a tired movie franchise:

I think I'll find another way
There's so much more to know
I guess I'll die another day
It's not my time to go

Maybe it’s because Madonna herself was 44 when she released the song: older, wiser, infinitely more tired but unable to let it any of it show lest she be declared past her prime yet again. It speaks to a defiant toughness, of having seen some shit, of having tried some shit and failed, of continuing to try instead of giving up and letting yourself just get run over by all the shit you can't control. American Life as an album is mid at best, after Ray of Light and Music literally changed the dance pop game at the end of the century, but “Die Another Day” stands alone as a big, cinematic, officially-electroclash track that divided critics at the time but remains a deep cut that even Madge herself can’t quite quit. 

#2 - "Ray of Light" Ray of Light (1998)

If "Vogue" is my true Madonna, her gorgeous, celestially enlightened Ray of Light era is an extremely close second.

Madonna found a true creative partner in British producer William Orbit, who only had a couple production credits before the insane smash Ray of Light turned out to be, winning multiple Grammys and reintroducing Our Madge to a new generation of dance floors bathed in electronic ecstasy. "Ray of Light" starts like any other late-90's Top 40 pop song would, with an upbeat electric guitar riff, then immediately drops you headfirst into a pulsing psychedelic beat threaded with manic energy and intense joy. It's wild to me that “Frozen” was the lead single, with its melancholic and appropriately icy feel, because “Ray of Light” isn't just the title track, it's also the true beating heart of the album, layered and swirling but with perfect control and a hint of self-awareness that keeps it from devolving into another cold, distant British-inspired club track.

#1 - "Express Yourself" Like a Prayer, 1989

"Come on, girls! You believe in love?! 'Cause I got something to say about it...and it goes something like this..." Engrave it on my tombstone, thx.

It is a truth universally acknowledged that if Madonna has a spoken intro to a song, it’s going to SLAP. “Into the Groove” introduced this concept, but “Express Yourself” perfected it.

I’m well aware that this is not a unique position for many Madonna fans, either: it’s a lot of people’s favorite song of hers for many reasons, not the least because it was a true feminist anthem a decade before the Spice Girls patented their “Girl Power” of the late 90’s. It's a song about sexual power dynamics within an established heteronormative relationship on the surface, sure, but the concepts can be applied to almost any area of your life that may be lacking a little empowerment. Don't go for second best [at your job/on a date/in your home/grocery shopping]! Make [your partner/family/friends/boss/dates/inner child] express how they feel, and then you'll know the love is real!

The ultimate bottom line is "You deserve the best in life/so if the time isn't right then MOVE ON!" Among the scores of women artists pining away for some guy, begging him to come back over decades of popular music, had there ever been such a clear clarion call to encourage healthy relationship communication as well as to stop fucking settling?

I think that's probably what made Madonna so controversial at the very heart of it all: she told women and other marginalized folks that you could get exactly what you want out of your life if you work hard enough, name and define your purpose and desires, and don't let stupid societal restrictions keep you from doing so. (Granted, this was achievable for her because she happened to be young, white, and hetero-normative but intersectionality wasn't really part of the cultural conversation in the 80's.)

Madonna is the perfect platform upon which our culture has projected so many of its insecurities and deepest, darkest fears and in turn she twisted and weaponized them right back to her own advantage. Is she perfect? Absolutely not–but that's part of her magic. Madonna owns her imperfections and deviations, and it's so cliché now, but it's true, as she stated during a pensive pause after several costume changes into the show: the most controversial thing she's done is stick around.


And so concludes this edition of The Enthusiast! Thank you for reading and if you're not already subscribed, you should sign up (it's free!).

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Express yourself, don't repress yourself!
LKH

And we're not sorry... It's human nature.