60 minutes of Madonna that show why she matters, as a musician and a cultural figure

The singer born Madonna Louise Ciccone has had one of pop’s most fascinating careers from a theoretician’s point of view—and fairly often over the past 35-plus years, her music’s been almost peerless, too. Madonna has remained a reliable hit-maker from the early 1980s to now, and yet it’s not that difficult to reduce her discography to a compact best-of, because she’s primarily been a singles artist, with songs that have sometimes worked better as self-defining statements than as cleverly catchy tunes. The challenge with Madonna is in keeping up with all of the ground she’s covered across three decades. Her primary strength has been in repackaging herself, getting out ahead of any critics’ attempts to define her by framing the conversation in advance. Through a one-of-a-kind fusion of sincerity and postmodern remove, Madonna’s been able to sing songs that put “music,” “sex,” “spirituality,” “fashion,” “fame,” “dance,” and “womanhood” into quotation marks, sparking conversations not so much about what they mean, but about what they mean to Madonna.

One of the more pivotal moments in Madonna’s story—and the history of modern pop, for that matter—doesn’t get discussed much anymore, even though it was all anyone was talking about back in 1992. In October of that year, Warner Books released the expensive coffee table tome Sex, featuring Madonna in various stages of undress, playing out kinky sadomasochistic scenarios. Sex was more arty than sexy, and aside from the eyebrows it raised and the outrage it provoked, it wasn’t an especially rewarding project in and of itself. But coupled with the previous year’s faux-revealing Madonna documentary Truth Or Dare, Sex raised complicated questions about just what fans really want from celebrities who use their eroticism as a marketing tool. The book lays it all bare, so to speak. And what it ultimately proved was that a fully nude Madonna was less alluring than the one from a few years earlier, who wore lacy bustiers and cooed coyly about virginity.

Since then, Madonna has played with the definition of “revealing,” seeming to expose her personal life in her songs while holding back just enough to leave fans wondering whether she’s just an actress, playing the role of a mega-star. And just as she’s tried to stay current with her image, Madonna has remained on top of musical trends, just avant-garde enough to give the impression—largely correct—that she knows more about what’s hot than any of her competitors. Her voice is a little too thin and nasal for a traditional pop diva, her performances lack a sense of abandon, and her albums have held to a fairly narrow path, sticking with dance music and dreamy ballads. But Madonna understands her genre, and she rarely buries the hook. Even mediocre Madonna songs sound like anthems, and the great ones have a rare indomitability.

The hour-long set of Madonna songs below isn’t a ranked list (although her best song comes first). It’s meant to be played straight through as a piece of music in and of itself: the ideal introduction to why Madonna matters, as a musician and a cultural figure.

1. “Ray Of Light” (1998)

Here’s Madonna’s career in a nutshell, in an exhilarating art-disco classic with religious overtones, released 16 years after her first single. Disguising any vocal weaknesses by treating the voice as its own pounding, elastic instrument—working in concert with the pulsing synthesizer and slashing guitar—“Ray Of Light” is a hot enough track that it could’ve worked with any singer. What makes it a Madonna song (besides her co-producing and co-writing it with EDM guru William Orbit) is its self-conscious defiance. At an age when most pop sensations would’ve slid into irrelevance, Madonna embraced a new Earth Mother role, proudly older and wiser, but still plugged in.

2. “Lucky Star” (1983)

The opener to Madonna’s debut album is unassumingly radical, bridging the gaps between synth-pop, club tracks, and the whole new genre of 1980s teen music that was about to follow in its wake. The bouncy beat—accented by what sounds like a dozen different kinds of electric keyboards and synths—makes “Lucky Star” sound giddier than it really is. Madonna’s vocal performance is both more controlled and earthier than the lovestruck adolescent she seems to be channeling in her lyrics, lending the song a lusty undercurrent. Later starlets would copy the sound of early Madonna, but in a way that felt more manufactured and less deeply felt (or shrewd).

3. “Material Girl” (1984)

Madonna constructed her image at first casually, and then carefully, over the course of her early singles and videos. “Material Girl” was the follow up to her controversial hit “Like A Virgin,” and in a way it’s an even bolder statement: an unabashed paean to conspicuous consumption. The video adds extra layers of irony to “Material Girl,” first by visually tying the song’s sense of entitlement to Marilyn Monroe’s unsustainable embodiment of 1950s glamour, and then by throwing in a twist ending that paints the singer as someone with more common tastes. But the song itself is so infectious that few really bought it as facetious. Almost instantly, the title became a Madonna nickname.

4. “Crazy For You” (1985)

In the middle of the run of singles from the Like A Virgin album, Geffen Records released this track from the Vision Quest soundtrack (after some contractual wrangling with Madonna’s label Sire) and gave the singer her first hit ballad. Madonna is most readily identified with her danceable cuts—perhaps because those are the ones that best suit both her voice and her sensibility—but she could do “soft” as well as any of the other acts that competed to score love scenes from 1980s movies. “Crazy For You” can stand toe-to-toe with Berlin’s “Take My Breath Away” and might even have a slight edge, because of Madonna’s personality and resume.

5. “Live To Tell” (1986)

An even more ambitious ballad than “Crazy For You” became the first single from Madonna’s third album True Blue, and signaled her willingness to push her music beyond the straightforward. The chorus follows a longer melodic line than usual, and works the title into the middle of a sentence rather than stressing it repeatedly. “Live To Tell” is also more mature in its subject matter than Madonna’s early hits, exploring dark secrets and bitter regrets in a way that suggests emotional depths merely hinted at before.

6. “Joan Of Arc” (2015)

Madonna’s latest album Rebel Heart sees her again collaborating with top dance music performer-producers like Avicii and Diplo, and holding to a harder groove, as has been her inclination over the last decade. “Joan Of Arc” is unusual in that it’s a hybrid of balladry and disco, working in service of the confessions of a scrutinized celebrity, who just wants some space to be flawed and human. This is one of the most strikingly personal songs Madonna has recorded, and deserves to be a hit if she releases it as a single.

7. “Everybody” (1982)

Madonna’s first solo recording never really became big outside of the clubs, but it’s still a fine statement of purpose: a rousing call to the dance floor, tinged with breathy desperation. In the many years that followed “Everybody,” Madonna would retreat over and over to the themes she introduces here, singing about the pleasures of dancing in a group and the desire to pair off with the hottest boy in the room. “Find a groove and let yourself go,” she tells the crowd, while she seems to be looking right in the eyes of the one she really means to seduce.

8. “Into The Groove” (1985)

Originally recorded for Madonna’s first big movie Desperately Seeking Susan—and then tacked on to a quick reissue of Like A Virgin a year after that album’s first release—“Into The Groove” finds her deep in club mode again, essentially remaking “Everybody” with a few more years’ experience. The song drops some of the pretense from its predecessor, as Madonna lets her prospective partner know that she’s very good at pleasuring herself, and that she expects him to get the job done for her if he wants to stick around. Madonna has recorded lots of songs about sex over the years, but “Into The Groove” is the most confidently joyous.

9. “Cherish” (1989)

For all the big statements and taboo-testing of Madonna’s fourth album, Like A Prayer, its best song was also its lightest and sweetest. “Cherish” practically gushes with romantic optimism in a way that few of her biggest hits do. The single that came right before it, “Express Yourself,” is more important in terms of its message of empowerment, but “Cherish” is a fine change of pace—pure pleasure, devoid of stridency.

10. “Hung Up” (2005)

Just as “Ray Of Light” gave Madonna second wind at the end of the 1990s, so “Hung Up” reenergized her career in the mid-2000s, selling over 9 million copies worldwide—her biggest international hit. The Confessions On A Dance Floor opener is a darker spin on “Cherish,” curdling the happy infatuation of the earlier song into creepy obsession. Musically, “Hung Up” is another return to Madonna’s club roots, and not in a way that seeks to reinvent or reconceptualize. This is just thumping dance music, hummable and crafty.

11. “Don’t Tell Me” (2000)

For the 2000 album Music—a follow-up to the acclaimed, career-rejuvenating Ray Of Light—Madonna was in a more actively experimental mode, splicing together dance music with modulated Americana. “Don’t Tell Me” is a reworking of a song by alt-folkie Joe Henry (who’s also Madonna’s brother-in-law), given a choppy beat and a heavily treated vocal performance, as though it were meant to be both the original track and the remix. It’s an example of a top-selling artist using her position to play around and having enough pop savvy to hit the charts.

12. “Take A Bow” (1994)

Madonna’s subtlest (and thus most unexpected) No. 1 pop single, “Take A Bow” is another of her sinewy ballads, this one co-written and co-produced with Babyface. Like “Live To Tell,” the song has a stunted chord progression in its verses but expands beautifully in the chorus, which winds around unpredictably. Just as surprising—and equally delightful—are the spiteful lyrics, which use a theatrical metaphor as a kiss-off to an arrogant lover. “The show is over, say goodbye,” Madonna whispers, softly but decisively.

13. “Sooner Or Later” (1990)

There are fewer better signposts of “Madonna in 1990” than this song from Dick Tracy, which represents so much of who she was trying to be at the time: movie star, timeless fashion icon, and girlfriend to Warren Beatty. “Sooner Or Later” is also a winning recording of Broadway songwriter Stephen Sondheim’s simplest retro pastiches. The quasi-soundtrack album that Madonna recorded to accompany Dick Tracy includes the non-movie song “Vogue,” her strongest effort to that point at placing herself in the tradition of pop culture’s grand dames. But “Sooner Or Later” makes the same point less aggressively: Just by singing a great song in a classic style, with plenty of her own va-voom, Madonna makes her case.

14. “Borderline” (1983)

In a career as long as Madonna’s, there are a lot of good entry points, but one of the best ways to “get” her is still to go back to the self-titled debut album, where she first struck a balance between innovation and simplicity, steeliness and fragility. The form of the Madonna hit “Borderline” is uptempo pop, but as with so much of Madonna’s work—especially in the early years—the content is much trickier. Between the faintly perturbed vocals and the anxious lyrics, “Borderline” is a love song that contains within it the seeds of a romantic break-up. It’s been that ability to work on multiple levels simultaneously that’s kept Madonna so viable for so long.

Total Time: 58:48