I received Madonna’s fourth studio album, Like a Prayer, on cassette for my 10th birthday. The liner notes were scented with patchouli oil to evoke the sensory experience of walking into a Catholic church, and you could smell it even through the shrink wrap. After devouring some cake, I rushed to my room to listen to the album.
It wasn’t like anything I’d grown up hearing on Top 40 radio, including Madonna’s own past hits, which I was only peripherally aware of. “Oh Father” sounded familiar, a cousin to “Live to Tell,” but it was darker and weirder. “Till Death Do Us Part” was more my speed, but the song’s lyrics were confusing and unsettling to my unrefined ears. Rolling Stone called it “as close to art as pop music gets.”
Despite its obvious lineage to classic pop and soul, Like a Prayer served as my gateway drug to alternative and indie pop—at least in spirit. The album defied contemporary trends: While Janet Jackson, Paula Abdul, and others were dabbling in house and new jack swing, Madonna deigned to take a more organic approach that better suited her confessional, autobiographical lyrics and tributes to her early musical influences.
Though Like a Prayer wasn’t Madonna’s last pop masterpiece, it remains a fulcrum in her discography, the point at which she pivoted away from being viewed as a “singles artist.” Somewhere, buried deep in a box of old records in my parents’ attic, the scent of patchouli is, like Madonna, still going strong. To celebrate the album’s enduring legacy, we’ve ranked all 11 songs from worst to best. Sal Cinquemani
11. “Act of Contrition”
In which Madonna reaches the proverbial pearly gates only to discover that her name isn’t on the guest list due to a clerical error. Constructed from a reverse-looped remix of “Like a Prayer” and prominently featuring the guitarwork of one Prince Rogers Nelson, the track showcases Madonna’s irreverent sense of humor and willingness to poke fun at her own stature as a pop deity who can, ostensibly, get a table anywhere she pleases. Cinquemani
10. “Love Song”
“Love Song” is a strange, albeit striking, bird. Madonna and Prince composed the song over an extended period of time by sending DAT tapes back and forth between Minneapolis and New York, where Madonna was performing on Broadway. As a result, the melody feels tentative, almost rudimentary—a stark contrast to the more fully developed songs that comprise the rest of the album but one that serves the ambivalent romance at the center of the song. Cinquemani
9. “Dear Jessie”
What sounds, on paper, like the makings of a cloying nursery rhyme—galloping percussion, giggling children, and psychedelic imagery of pink elephants, singing mermaids, and flying leprechauns—is actually a bittersweet reminder of our fleeting innocence and imagination. A whimsical baroque-pop lullaby punctuated by playful orchestral swells, regal trumpets, and Beatles-esque tempo-shifts, “Dear Jessie” is a testament to the magic of Madonna’s work with composer/producer Patrick Leonard. Cinquemani
8. “Keep It Together”
On the Sly and the Family Stone-inspired “Keep It Together,” Madonna convincingly took on pop-funk. The slap bass and jangly guitars (courtesy of an uncredited Prince) make this one of the more upbeat, hummable listens on the album, but it’s no less packed with feeling. Madonna’s affirmation of family bonds is uncharacteristically sweet and vulnerable: While she’s alluded to a strained relationship with her father over the years, she pays tribute to their deep bond with a heartening reminder, especially in the wake of her divorce from Sean Penn: “Daddy said, ‘Listen, you will always have a home.’” Paul Schrodt
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7. “Spanish Eyes”
When I interviewed Patrick Leonard in 2018, I took the opportunity to ask him a question that had been nagging me for years: What is “Spanish Eyes” really about? I’d always interpreted the inner-city violence depicted in the song’s lyrics as a metaphor for the AIDS crisis: “Stand your guns against the wall/Who’s next in line to fall?” (in the liner notes, the word “guns” is replaced with “arms,” rendering the original intent even more ambiguous). Leonard told me he believes the song is about gang warfare but conceded that Madonna’s lyrics can often have multiple readings. It speaks to the power and conviction of her performance that the song feels so profoundly personal, as she reaches the upper limits of her range to beg a God she doubts even exists to spare the life of a man she loves. Cinquemani
6. “Promise to Try”
A heart-wrenching piano ballad about the death of Madonna’s mother, “Promise to Try” evades excessive sentimentality due in large part to the singer’s raw, unvarnished vocal performance. Madonna alternately refers to herself in the first and third person, reflecting a deep trauma that’s almost dissociative. “Don’t let memory play games with your mind/She’s a faded smile frozen in time,” she sings at one point, capturing both the fog of childhood memory and the ephemerality of life itself. Cinquemani
5. “Cherish”
“Cherish” is a beacon of light, a spritely and slyly referential dollop of “True Blue”-esque doo-wop swimming atop the engorged baroque pop that is Like a Prayer. The song’s radiance stems from Madonna’s sense of foresight—her understanding that this might just be her last chance at conveying such a sweet and uncomplicated sense of joy. It’s as if she can see the more duty-bound chanteuse of Erotica waiting to step in to rewrite the story of Romeo and Juliet in the context of an era, unlike this one, that’s less complacent about how our fears have hijacked our desires. Ed Gonzalez
4. “Till Death Do Us Part”
How well this song has aged sonically may be at the mercy of Patrick Leonard’s then-state-of-the-art 1988 Yamaha keyboards, but the producer’s pointillistic use of synthesizers is, like on “Open Your Heart” before it and “I’ll Remember” after it, a thing to behold. No more so, however, than Madonna’s autobiographical account of her turbulent marriage to Sean Penn. In a song filled with lyrics that sting, this is but one: “You’re not in love with someone else/You don’t even love yourself/Still I wish you’d ask me not to go.” That barely perceptible whirring engine at the very end of the song is the sound of her going. Cinquemani
3. “Oh Father”
If “Oh Father” doesn’t touch the pop-gospel magnitude of “Like a Prayer,” on which the choir endows Madonna with strength and confidence, that’s by design. On this inversion of the Lord’s Prayer, the singer seeks those things out for herself. Patrick Leonard’s genteel production cedes as much power to Madonna as possible. It’s not the track’s soaring violins or the cherubic background vocals that do the heavy lifting here, but the wounded charge of Madonna’s sense of remembrance, which is so acute as to carry her into a realm of spiritual salvation. Gonzalez
2. “Express Yourself”
It was David Fincher’s Metropolis-inspired music video for 1989’s “Express Yourself” that introduced the world to Shep Pettibone’s remix, which, aside from the lethargic come-and-git-it cowbell that intermittently takes Madonna from the church steeple and straight onto the prairie, matches in its uptempo beat the soulful fervor of the singer’s call to arms. The album version evokes something altogether more subversive: Fritz Lang’s robot Maria hanging out inside a Detroit dance hall, forcing men to their knees as the big-band sound rocks the house. Gonzalez
1. “Like a Prayer”
With an atypical structure in which the drums drop out completely during each verse and the chorus is all but abandoned halfway through the song in favor of ad libs and gospel choiring, what’s now considered a perfect pop song seemed more fit for a church than Top 40 radio in 1989. Though she’d evoked religion before, most notably with heaps of rosary beads dangling between her décolleté, it was, perhaps, inevitable that with a name like Madonna, the so-called Material Girl would more seriously explore the faith with which she was so strictly raised. But while there have been about as many interpretations of the song’s lyrics as there are remixes—she’s singing about God, she’s singing about giving a blowjob, she’s singing about giving God a blowjob—“Like a Prayer” begs for a more refined reading than a conflation of spiritual and sexual ecstasy. Cinquemani
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