Madonna's done it all. And we've pretty much covered it all. So when we sat down to decide the best way to celebrate the anniversary of Madonna's debut album, released 30 years ago tomorrow, we elected to dig up some of the forgotten or unheralded gems scattered liberally throughout her three-decade-spanning catalogue rather than predictably rank her best albums, singles, or videos—which we've more or less done on various other lists over the years anyway.
With the exception of one B-side, one compilation cut, and one remix, all of our picks can be found on a Madonna studio album—a testament to the singer's strength as an album artist, particularly in the '90s. These are songs that, in a more adventurous world, could have been hits, and in some cases where the releases were nixed last minute, almost were, their breadth and depth reflective of an artist unwilling to allow herself to be defined. And just for shits and giggles, we ranked 'em.
#15. "Physical Attraction"
"Maybe we were meant to be together/Even though we never met before." If that doesn't sum up the relationship between Madonna and her instant fanbase circa her self-titled debut, I don't know what does. "Physical Attraction" finds Madonna, still believably coquettish and naïve at this early point, tellingly offering her permission to take things to the next level. The girl was in the driver's seat from day one, and never slid aside for anyone. Eric Henderson
#14. "Easy Ride"
The literal and figurative denouement to both 2003's divisive American Life and, more broadly, Madonna's folktronica period, "Easy Ride" is the ultimate exemplar of Madge and Mirwais's obsession with marrying acoustic guitars, squelchy synths, and deconstructed orchestral arrangements. Her vocals start off raw, nearly unrecognizable, and eventually grow fuller and richer until she admits what nearly every move of her 30-year career attests to: "What I want is to live forever." Sal Cinquemani
#13. "Over and Over"
This hi-NRG track from Like a Virgin is an early snapshot of a larger-than-life personality, introducing themes—racing against time, perseverance, and overall (blond) ambition—that would grow ever more pervasive in Madonna's lyrics as she got older and more famous. The frenetic extended version, from 1987's You Can Dance remix album, amps up Nile Rodgers's original production with supersonic synth washes, time-stamped keyboard percussion fills, and—because why the hell not?—ringing alarm clocks. Cinquemani
#12. "Gang Bang"
Even before she splattered blood across three-story projection backdrops during her MDNA Tour, the gruesome imagery, the seemingly contemptuous snatches of dubstep, and the purely exploitative application of violence in what is otherwise an exercise in horror as fashion statement ("He deserved it") within the Nancy Sinatra-swiping "Gang Bang" already positioned Madonna right alongside the new French extremists. There is no statement here, no empowerment, no redemption. Just a thrilling moment of reckless respite, the sort of indulgence only someone who has attained a certain level of renown can truly savor. Henderson
#11. "Has to Be"
Ray of Light may have marked the queen's return to her EDM throne, but it was her reunion with longtime songwriting partner Patrick Leonard, as well as producer William Orbit's more subdued ambient soundscapes, that elevated the project above a mere electronica cash-in. Putting the law of attraction to the test, "Has to Be," the meditative B-side to "Ray of Light," is an anguished appeal to the gods above from the loneliest, most famous woman on Earth. Cinquemani
As I wrote in my review of Erotica upon its 15th anniversary, "Waiting" is the ultimate masochism, one that's entered into with full knowledge of what the emotional consequences will be. The very first lyric, "Well, I know from experience that if you have to ask for something more than once or twice, it wasn't yours in the first place," which Madonna utters with the same amount of interest a star of her stature might apply to buying a new pair of shoes, also happens to be one of the best opening lines to a pop song since "I guess I should have known by the way you parked your car sideways that it wouldn't last." Cinquemani
#9. "Sky Fits Heaven"
This Ray of Light track is famous for being lyrically inspired by British poet Max Blagg's 1992 poem "What Fits?" (later used in a Gap jeans commercial), but the song is a marvel not for Madonna's new-age pontifications, but for its heavenly hook and William Orbit's impeccable use of both analog and digital technologies, marked by expressive electric guitars and explosive drum fills constructed from tiny fragments of sound. Cinquemani
#8. "I Want You"
Madonna's haunting rendition of Marvin Gaye's "I Want You" is, if not more soulful, infinitely more desperate than the 1976 original. The confidence and determination in Gaye's voice is replaced here with the kind of naked vulnerability Madonna perfected on Bedtime Stories a year earlier. Her feat is no doubt aided by the song's transformation from a conga-accented disco number into a more languid trip-hop track, courtesy of Massive Attack and producer Nellee Hooper. Cinquemani
From Marcel Proust to the more contemporary poet Carol Ann Duffy, Madonna has always drawn on literary influences in her lyrics, but it was of particular note on 1994's Bedtime Stories, in which she artfully co-opted the work of George Herbert on "Love Tried to Welcome Me" and Walt Whitman on "Sanctuary." On the latter, which musically draws inspiration from Herbie Hancock's "Watermelon Man," she boldly and cleverly pairs a passage from the Book of Genesis with Whitman's "Vocalism," effectively likening her existence prior to meeting her object of obsession to that of the Earth before God. Cinquemani
#6. "Inside of Me"
With full, round production by Nellee Hooper, "Inside of Me" on the surface sounds like a warm, intimate sauna of slack slow jack built on a foundation of Aaliyah and the Gutter Snypes samples, but radiating a sensuality that's all Madge. But like every track on her prior album, Erotica, this song's breathy hedonism masks an inner devastation: Underneath those tear-stained suggestions of sex mournfully deferred is actually a heartfelt tribute to her mother. Staring down a crossroads in her career, Madonna couldn't help but make grief sound like fornication. Henderson
#5. "Till Death Do Us Part"
How well the 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
#4. "Thief of Hearts"
Let there be no mistake: Madonna, at the peak of her imperial stage, was no benevolent dictator, and the full-out house assault of "Thief of Hearts" could serve as the national anthem for her jaded kingdom. Ain't no coup d'état in this house. Just hard beats (if ever there was a litmus test for one's tolerance of Shep Pettibone's particularly monolithic production values, this is it), harder beatdowns ("Which leg do you want me to break?"), and the hardest lesson Madonna has ever had to bear: that the "Little Miss Thinks-She-Can-Have-What-She-Wants" she so mockingly sings about is herself, her own worst enemy. Henderson
#3. "Sooner or Later"
For a performer as impenetrable as Madonna likes to make herself out to be, there was no hiding the way her expensive baubles vibrated tremulously from her ears when she performed Stephen Sondheim's Oscar-winning song from Dick Tracy during the 1991 Academy Awards. It was a "Breathless" performance for what is otherwise one of the most unabashedly confident songs in Madonna's back catalogue, a rip-roaring jazz pastiche that added another layer of brash shading to Madonna's Marilyn caricature. Henderson
#2. "Impressive Instant"
Perhaps the closest French quirk-house producer Mirwais got to no-glitch disco in his stint with Madonna, "Impressive Instant" was that close to being released as Music's fourth single, and did end up topping the dance charts via DJ promo. With a distorted bassline that sounds like fire dancing from the depths of Hades, and Madonna tossing aside her Ray of Light Mother Earth-isms in favor of "I like to singy, singy, singy like a bird on a wingy, wingy, wingy," the song is one of her most blatant U-turns back into the welcoming arms of dance music. Henderson
#1. "Secret Garden"
The day she ever stops "wanting, needing, waiting" will never happen, a point Madonna drives home at the climax of Erotica when she muses, "I wonder when I'll start to show/I wonder if I'll ever know/Where my place is/Where my face is." Andre Betts's shuffling breakbeat and the jazzy piano and sax flourishes serve as a musical palate cleanser following Shep Pettibone's highly icy house beats. But make no mistake, she's no closer to wrapping up this story, and the way her discontent radiates even through lines about how "the sun has kissed me" is a lens through which her entire rocky career can be viewed. Henderson