43. Madonna, “Open Your Heart.”
David Byrne once sang, “Watch out, with that attitude you might get what you want,” and it feels as if Madonna has made a career of realizing that ambition by any means possible. It’s funny to think that “Open Your Heart” could have ended up with someone other than the Material Girl. Yes, Cyndi Lauper might have spun something altogether more poignant from this unabashedly sincere and playfully metaphoric love song, but the conviction Madonna reveals throughout, as exhaustible as Patrick Leonard’s fluttering rock-dance bassline, finds her in a strikingly confessional light. As in the song’s polar opposite, 1993′s “Bye Bye Baby,” an anti-love song in which she coyly makes the man do the chasing, Madonna was and always will be credible only at her most naked. EG
28. Madonna, “Live to Tell.”
Madonna’s first and, arguably, most dramatic reinvention was scored by the spare and haunting ballad “Live to Tell,” which wasn’t just a daringly demure introduction to her third album, but also posed a challenge to pop-radio programmers keen on instant gratification: The song begins with almost a full minute of music before the singer starts to tell her tale, and includes abrupt key changes and a half-minute midsection in which nearly all of the music drops out. Of course, it worked like a charm, and “Live to Tell” launched a fruitful professional relationship between Madge and producer Patrick Leonard that would last for more than two decades, and set the stage for the fearlessly autobiographical material to come. The song features one of Madonna’s richest vocal performances, full of soul, yearning, and hurt, with lyrics that can surely resonate with anyone who’s ever endured a detention of silence—self-imposed or otherwise. SC
26. Madonna, “Into the Groove.”
Leave it to Madonna to make the campy, throwaway, opening lines of a B-side into a career-defining mission statement. She’s at her most coy as she speaks, “You can dance, for inspiration,” over the first few bars of “Into the Groove,” the theme from Desperately Seeking Susan and, somewhat inexplicably, the B-side of the considerably less brilliant “Angel.” But who cares that one of Billboard’s technicalities kept the song from charting on the Hot 100: Madonna’s never come up with a more apt assessment of how her music works best. Whenever she’s lost her way artistically, she’s headed back to the dance floor to get her head right. JK
16. Madonna, “Express Yourself.”
It was David Fincher’s music video for this smash from Like a Prayer that introduced us 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 the soulful fervor of the singer’s call to arms. But MTV doesn’t play music videos anymore, and when I’m listening to this song on my iTunes, it’s the original album version I prefer, as it 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. He has it coming in both versions, but in Stephen Bray’s original Madonna comes fearlessly out of nowhere. EG
7. Madonna, “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, what’s now considered a perfect pop song seemed more fit for a church than Top 40 radio at the time. 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 brainy conflation of spiritual and sexual ecstasy: It’s a song about love. SC
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