10. Madonna, “Vogue.”
Much has been written (specifically on this site) about the cultural impact of the appropriation of queer and nonwhite motifs in Madonna’s “Vogue,” so I’ll focus instead on the song’s musical archaeology and influence. Lest I completely ignore its substance, Madonna’s message is clear (“Beauty is where you find it”), but the track’s origins are part and parcel with its star’s mining of gay club trends and Old Hollywood: Inspired by the Salsoul Orchestra’s “Ooh, I Love It (Love Break)” by way of Danny Krivit’s remix of MFSB’s “Love Is the Message,” the song has a family tree that even includes producer/DJ Shep Pettibone’s remix of Janet Jackson’s “Miss You Much” and serves as a sort of musical map of disco. Pettibone recorded “Vogue” with Madonna as a B-side for her single “Keep It Together,” making its impact all the more impressive (it would go on to inspire a glut of pop-house copycats) and begging the question: If disco died a decade earlier, what the f*ck was this big, gay, fuscia drag-queen boa of a dance song sitting on top of the charts for a month for?
16. Madonna, “Ray of Light.”
Once the Material Girl made it her mission to bring electronica to the masses, she could have named her collaborator. Her decision to work with William Orbit shows that, for all the flack she’s faced for “appropriation,” her interest in underground dance music is deep and not wholly commercial. Madonna discovered techno just as she turned 40 and took up Kabbalah, and listening to “Ray of Light,” it’s easy to imagine Madonna finding in rave culture not just a new image, but a way of expressing her spiritual awakening. The beat is restless and Madonna sings breathlessly, but she exudes contentment: “I feel like I just got home!” Her emotional warmth is what establishes the song as a standout single even in a catalogue as replete with classics as Madonna’s.
34. Madonna, “Erotica.”
Madonna accepts the burden of her throaty, spent-from-touring voice, which makes Erotica’s taunting, aggressive lyrics—an elaborate exploration of sex, from seduction to disease—feel unmistakably honest. The title track, whose opening put-a-record-on scratchiness mirrors that of Madonna’s most divisive instrument, is the singer’s invitation to the dance, a slithering, sinister snake rising from a gaudily ornate chalice. The beats are, by design, hypnotic—at once alluring and devious. With “Erotica,” Madonna promises to get you off, but not without giving you something.
36. Madonna, “Deeper and Deeper.”
Among Madonna’s finest achievements, the angsty pop anthem “Deeper and Deeper” is both an acute distillation of Erotica’s smut-glam decadence and the singer’s lifelong blond ambition. The song, like its video, practically plays out as an autobiography of the singer’s life: Atop sambalicious disco, Madonna delivers a burning, poignant fairy tale of yearning and escape in which she plays both Little Red Riding Hood and the Big Bad Wolf. Armond White once praised Madonna for how she took “outsider art inside herself”—which is to say, justified it by personalizing it. The uncontrolled, fierce tension of the song derives from the feeling that Madonna is taking a plunge into some hedonistic abyss of her own liberated, uninhibited making.
42. Madonna, “Secret.”
Despite the common misconception that she often sings about sex, Madonna’s songs aren’t always sexy. “Secret” is perhaps the finest exception to that rule. As it slinks along a simple R&B backbeat and an unfussy acoustic guitar figure, “Secret” is also one of the most organic-sounding singles of Madonna’s career, taking its sweet time to get where it’s going and not giving up too much along the way. The arrangement gets off on being withholding, and, at least for one glorious single, so does Madonna: When she sings, “You knew all along/What I never wanted to say,” she sounds positively rapturous.