Bill’s Top 10 Madonna Albums
In my life, there are few events I’ve ever been as excited about as I have been for The Celebration Tour. The tour was originally scheduled to begin in Vancouver, BC, and make Seattle its second stop. That would’ve given this Madonna fan and scholar an early glimpse at her only retrospective tour, a journey through forty years of Madonna’s career, a gift to fans and a reminder to everyone else that she has always been an unstoppable force in popular culture. But a sudden illness forced her to postpone the American leg of the tour. Hoping to immerse myself in the concert and avoid spoilers from the thousands of videos posted to social media from previous stops, I’ve been focused calligraphing a shirt with my favorite lyrics with the persistence of a Buddhist monk creating a sand mandala, revisiting her studio albums, and, revealing one at a time to friends via social media, creating my list of the Top 10 Madonna albums. Here’s the list (and my increasingly long reflections…because with each album, there’s just more and more to say).
Number Ten: American Life
Madonna took on the system, or really all the systems - government , Hollywood, families, relationships, gender dynamics - by bringing social critique to the dance floor and serving up a mix of lovely, innovative, and introspective ballads with a dash of James Bond.
Number Nine: Like A Virgin
Nearly every track on the album is iconic, either essential to the development of Madonna’s persona or a perfect reflection of this corner of the 80s. Hype around it typically focuses on the more, dare I say, “material” aspects of the album’s aesthetic, but too many listeners miss the artistic experimentation happening in the album which were among the early successes in bridging more mainstream pop and underground or alternative scenes. The accompanying videos, too, are pioneering in developing the then-new medium of the music video: “Material Girl” blended homage and irony, and “Like A Virgin” was 80s fantasy perfection. I can see the imprint of these tracks and videos today on performance and production across genres.
Number Eight: Madonna
Madonna’s self-titled debut album introduced a new kind of female pop star and inspired a generation of Madonna Wannabes who adopted her eclectic, layered, irreverent style. Most of the songs are known so well that folx don’t stop to notice the earnestness of the lyrics. I can’t listen to “Borderline” without imagining a deeper, harder story - maybe it’s a painful reflection of a relationship impacted by mental illness - or the anthemic “Holiday” as a youthful plea for peace. “You can turn this world around…” And the song’s video infuses Martha Graham-inspired modern dance with dance music, one of the earliest of countless transgressions across the boundaries of different media and influences.
Number Seven: Confessions on a Dance Floor
Confessions both capped an era of significant output (1998’s Ray of Light, 2000’s Music, 2003’s American Life) and signaled an artistic shift. I think it’s an extraordinarily revealing album, pointing directly to lifelong and more recent influences (among them: disco, electropop, punk, Yemeni Jewish mysticism, girl power anthems), but more than referents, the tracks excavate the raw joy and anger that more saccharine homages fail to tap. It’s a no-skip, seamless album that features some of her loveliest melodies. The album inspired my favorite of her tours, and the image that she sculpted (including and especially that flattering pink leotard for the dance studio solo in “Hung Up”) was a middle finger to the industry and public who thought the 47 year old creamy-smooth pop icon goddess should hang up her tights and retreat into old ladyhood.
Number 6: True Blue
True Blue is the penultimate of what I think of as the “foundational albums.” If Madonna and Like a Virgin opened the door, True Blue marked Madonna’s entrance and secured her place at the table. It also hinted at the mastery she’d serve with Like A Prayer and “Vogue” a few years later. She’d already carved a niche with her sound and her image, but in True Blue, the songs lean into bolder storytelling, like the misty “La Isla Bonita,” the provocative “Papa Don’t Preach,” and the enigmatic “Live To Tell.” Her innovation in storytelling extended to the videos accompanying the album, like the deceptively powerful “Open Your Heart,” a stylized dismantling of the male gaze. True Blue is also what drew academics in various disciplines to recognize that Madonna wasn’t just a flash-in-the-pan reflection of pop culture and the music industry but a major player, creating something new, and defying conventional categorization.
Number 5: Madame X
Her most recent studio album, Madame X is impressive, sophisticated, and forward-thinking. The name, a nod to her most recent reinvention (she added Madame X to Madonna Louise, Veronica, Dita, Esther, and the countless layers she’s peeled back over the years), is both provocative (summoning the image of an international woman of mystery) and sentimental (a callback to the nickname Martha Graham presciently gave her to reflect her capacity for identity-shifting). The music is ambitious, reflecting smart collaborations (Maluma, Anitta, Quavo, Swae Lee), new influences (like her years in Portugal and contemporary socio-political crises), and experimental. The videos accompanying the album are among the best she’s produced, including the rattling “God Control” (inspired by the Pulse nightclub shooting), the moving “Batuka” (which features the Batukadeiras Orchestra and contemplates the history and ongoing impact of the slave trade), and the stunning “Dark Ballet” (a nonlinear meditation on Joan of Arc, transgender - and by extension any transgressive - identity, and institutional oppression; in my mind the most powerful video she’s made since “Like A Prayer”).
Number 4: Like A Prayer
If you’ve ever been near me when the video for “Like A Prayer” plays, God bless you. You’ve probably been subjected to my mini-lecture about the innovations of the video, about its dialogue between medieval mysticism and modern injustice, about the controversial and canceled Pepsi deal, and about why this was a ground-shifting moment in popular culture. Beyond that monumental video and the song that inspired it, the album in its entirety is top tier and cemented Madonna’s status in the upper echelons of culture-makers. The album features one of my favorite collaborations: “Love Song” marked the intersection of two geniuses of the era, Madonna and Prince. Even the mostly-forgotten tracks later in the album constitute a trove of hidden gems that, if nothing else, perfectly capture the end of the 80s. Her team was on a roll with videos, too, like “Express Yourself,” which invoked Metropolis and inspired one of the sleekest, sexiest videos ever made, and the Herb Ritts-directed video for “Cherish,” which seemed to birth a whole genre of sexy black & white frolicking on the beach that dominated everything in print media from perfume ads and Abercrombie catalogs to senior portraits. Paired with the phenomenon that was “Vogue” (released a year later as a single and then with I’m Breathless, which accompanied the film Dick Tracy), it marks a moment in pop culture: there was life before Like A Prayer, and life after.
Number 3: Erotica
1992 was a very good year for music, and Madonna was ready to flex. Riding high on the successes of Like A Prayer, “Vogue,” and The Blond Ambition Tour, Madonna’s approach shifted from shocking provocation (her explicit sexuality and casual Catholicism inspired most of the pearl clutching) to bold assertion (stymying the critics who’d hoped to shame her into conformity). Criticism spiked with the sublime “Justify My Love,” whose accompanying video depicted a highly stylized series of sexual fantasies. For journalists and concerned parents everywhere who couldn’t figure out how to criticize “Vogue” without sounding homophobic, “Justify” was an easier target.
Some celebs bow to that kind of pressure and reform their images. Madonna responded by publishing the infamous Sex book and dropped the Erotica album. To some, it was a stunt, a middle finger to prudish critics. To others, it was a bold political statement or artistic experiment. To a closeted kid in an all-boys Catholic high school, I was empowered and reassured - not by the Sex book (I never read it until grad school) but by Madonna’s response to criticism about it. Madonna was badgered by interviewers hoping for some confession or relenting, but her replies were consistent: she was presenting reality - people’s desires, needs, and feelings. HER desires, needs, and feelings. And for me, though deep in the closet, I could hear in the album that she was presenting MY desires, needs, and feelings. The rest of her queer following, out and closeted alike, must’ve felt the same - it invited loyalty and enthusiasm from LGBTQ fans who saw our desires, needs, and feelings being celebrated (not just tolerated, in the don’t-ask-don’t-tell era). Every track in some way explores owning one’s own sexuality, power, desires, and needs. It’s a message we needed in 1992 and still need today.
On top of all that, the music is just really fucking good: Her cover of “Fever” is sexy as hell and revives an old standard with new beats. There aren’t many songs in the pop canon better than “Deeper and Deeper” and “Rain.” And “In This Life” is a poignant snapshot of the pain and grief that came as the AIDS epidemic was peaking in the US.
Number 2: Ray of Light
At this point, you might be wondering, Why is Bill so obsessed with Madonna? It’s a fair question. In part, it’s an OGT (obviously gay trait), along with my youthful devotions to Angela Lansbury, Bernadette Peters, musical theater, and The Golden Girls, those quirks that developed long before I understood what “gay” was and yet told the world who I was. I was 7 when Madonna released her first studio album, and, growing up in a house without cable, it was only on the 4pm music video hour on channel 44 that I could see her early videos. Despite such limited and sporadic glimpses, something deep in my soul told me that she was my girl. My obsession started early…and quietly. Just as I couldn’t explain my obsession, I couldn’t explain why I knew to keep it secret.
Ray of Light was released in the spring of my senior year of college, and as I prepared for a move to start divinity school in Boston, it provided a soundtrack for my life. Inspired by a major change in her life (parenthood) and infused with insights gleaned from her increasingly diverse spirituality (this was the peak of her engagement with Hindu practice and anticipated her deep dive into Kabbalah), the album felt like a gift particularly to me. Always immersed in her native Catholic symbolism, now Madonna was a spiritual traveler and a touchstone for me as I struggled to understand religious diversity and embody pluralism.
In a course on the intersection of eroticism and mysticism, I decided Ray of Light would be the focus of my independent research. I had no idea what kind of wormhole I was about to slide into or that on the other side I’d arrive in the magical land of Madonna Studies, the interdisciplinary academic dialogue among theologians, sociologists, feminist theorists, anthropologists, philosophers, media critics, and others that explored Madonna’s art and impact. My final product was a 28-page paper with a title paraphrasing a key lyric, “Traveling Down Her Own Road:” - because every legit academic essay had a colon and subtitle - “A close reading of Madonna’s Ray of Light.” My professor loved it, and that A meant that I could say I have a master’s degree because of Madonna.
Since then, though I’ve lost the original paper to a hard drive I can’t access anymore, I’ve built on that research and spun it into lessons for my high school classes, professional development workshops for colleagues, a 5-week symposium, and last summer a one-hour keynote focusing on the evolution of Madonna’s queer allyship to launch the Pride observances in a division of Microsoft. I’m buoyed not just by my personal passions but by the fact that Madonna has moved and continues to move the needle in American and global culture. That’s just a fact, and, whatever your attitude to her artistically or personally, it means she’s worth paying attention to. I like to explore how she moves the needle, how her music and the videos and tours spawned from it demonstrate social commentary, cultural parasitism (actually, “mutualism,” to be precise), reinvention, and her role as a catalyst for postmodernism. And it all began with Ray of Light.
My own personal history aside, Ray of Light is a perfect pop album. Her partnership with William Orbit produced a sound that dominated the era and others chased to recreate. Each track stands alone, but I enjoy listening to the album most in a single sitting.The heart of the album isn’t a dance single or mega hit - it’s an obscure Hindu prayer, preceded by “Sky Fits Heaven,” which is as much a theological treatise as it is a pop track. The transition between these tracks is so sublime it gives me chills every time.
Number 1: Bedtime Stories
Now, when it comes to the top albums, I’m splitting hairs. If I were stranded with only one album to listen to, as the ice breaker goes, I’d happily bring Madame X, Like A Prayer, Erotica, Ray of Light, or my #1. Each demonstrates the mastery of the collaborative collective of musicians, choreographers, producers, stylists, and others who are fueled by and rely on Madonna’s talent and vision. And I should note that this hasn’t been a list of her “best” albums springing from some technical rubric. If you’ve disagreed with any of my rankings, well, as Dorian Corey might say, “hooray for you,” but I don’t really care. Make your own list, and I’ll gladly cheer you on. These rankings reflect not just the artistic merit of each album but also where and how I met it, how it impacted and continues to reveal itself to me, and good old-fashioned gut instinct.
I came late to Bedtime Stories. Sure, a few tracks always stood out. “Take a Bow” was one of those songs you played at moments that needed closure. The opening guitar strums and melodies of “Secret” are iconic and distinctive. “Human Nature” is one of her most effective (what I think of as) “bitch ballads,” those autobiographical songs that not-so-subtly let her haters know (to borrow a later lyric), “Bitch, I’m Madonna.” And that “Human Nature” video…it was released at the end of my first year in college, and let’s just say, it was an awakening. I even dressed in the style of the video for my “A Very Madonna New Year’s Eve” party to ring in 2001.
Yes, I hosted a Madonna-themed party and even awarded prizes for my guests’ amazing costumes which reassured me that I wasn’t alone in my fascination. The only criterion was that the outfit was inspired by Madonna, someone in Madonna’s life, or or some aspect of her career. What were the winning looks, you ask? Third prize went to friends who arrived as Guy Ritchie and “Don’t Tell Me” Madonna, cowgirl chic and all. Second prize went to a friend who arrived in a full Dick Tracy costume. And the Grand Prize to a friend who arrived as Dennis Rodman, donning an enormous wedding dress, hair sprayed green, and skin covered in tattoos.
Over time I came to appreciate the blend of styles throughout the album (R&B, hip hop, electropop, dub), a reflection both of her collaborators on the album (Nellie Hooper, Babyface, Dallas Austin, Björk) and the swirl of sounds in the mid-90s. Amid my research in grad school, deep analysis allowed me to notice the subtle innovations and layers in each track. But it wasn’t until my mid-30s that I started to really hear and internalize the core messages of the album, captured in two key lyrics from the album: “express yourself, don’t repress yourself,” and (my favorite lyric from her entire oeuvre) “words are useless, especially sentences.” In Madonna-ese, I faced a moment for my own reinvention. After the end of an 8-year relationship and uprooting from Boston to NYC and then DC, Bedtime Stories gave me vocabulary to identify who I’d been and explore who I could be. Those lyrics became frequently recited mantras and played no small part in a personal and professional overhaul that has shaped my path to this moment.
In many ways, Bedtime Stories fulfilled the promise of Erotica, delivering the sensuality and eroticism many expected. If there’s a hint of anger underlying Erotica, Bedtime Stories is built on a foundation of “fuck it” that gave her (and countless female artists that followed her) the freedom she deserved. The result is an album of honesty, mystery, and recognition that some things are well beyond the world of words and human capacities. To me, the album is a pivot enabled by that freedom. Bedtime Stories both captures the growth and mastery that she’d experienced as a performer and as a producer up to that point and plants the seeds that would become Ray of Light and later masterpieces.
My favorite part of the album is the transition from “Sanctuary” to “Bedtime Story.” Like the pairing of “Sky Fits Heaven” and “Shanti/Ashtangi” on Ray of Light a few years later, this is the heart of the album. “Sanctuary” blends Christian spirituality with erotic and sensual beats and language. Like “Like A Prayer,” it stands at the intersection of mysticism and eroticism and is a reminder of the deep hunger for both in the human heart. The music fades but doesn’t break before transforming into the dub beats of the title track. Part manifesto, part make-out-on-the-dance floor music, it’s a gorgeous, restrained, ambient, and uplifting piece of music.
But let’s talk about the video. The most expensive video produced up to that point, it explores Jungian psychology through the art of female surrealist painters. It also employed early CGI animation. Though you can tell on the HD screens of today, in 1995 it was seamless and magical. In all the contexts I’ve shared the video (lessons with students, professional development workshops, symposia, impromptu lectures to unwitting guests in my living room) it’s the one I look forward to most because the combination of Madonna’s music (with a heavy helping of Björk), surreal art, Jungian psychology, and the sheer of beauty of the video inspires the best reactions - from surprise and delight to shock to awe.
