This weekend marked the 30th anniversary of Madonna’s first hit song, “Holiday.” The joyful tune turned Madonna into the still-reigning queen of pop, so I had to (just had to) collect my picks for the thirty subsequent singles that best define her career. I'm not saying they’re her best songs, per se. I'm not sure it's how I would rank my personal favorites. Even some memorable hits just couldn’t fit on the list. (Apologies to “Borderline” and “La Isla Bonita.”) But they are, if you ask me, the tunes that best encapsulate everything about her. They're the "most Madonna." Take some time to celebrate (just one day out of life) a legendary career.
30. Secret (1994)
Madonna has released over 70 singles in her career, and holds a record for the most top ten hits by any artist. With a catalogue that big, it’s easy to forget plenty of gems. Its slinky R&B groove made “Secret” something special, even if it’s not remembered for an accompanying scandal or bawdy “moment.” We like to talk about her ability to produce controversy and headlines, but at the end of the day, here’s what Madonna makes best: pop music.
29. Bad Girl (1993)
By the time “Bad Girl” came out, Madonna was bruising from the pig-pile backlash to her most overtly sexual period. Ironically the schoolmarm squawking about her carnal obsessions caused many to miss this minor hit about a woman whose nymphomania masks something sadder: “Bad girl, drunk by six, kissing some kind stranger’s lips. Smoked too many cigarettes today, I’m not happy when I act this way.” The cinematic video, directed by regular collaborator David Fincher (Fight Club) and starring Christopher Walken as the grim reaper (naturally), reinforces that while Madonna is indisputably sex-positive, her outlook on the complex emotional intersections of sex, power, and self-confidence is not without nuance.
28. Rain (1993)
That Madonna’s “not the best singer” is a qualifying statement that manages to work its way into almost every critique of her music. (Though she actually sings better than many newer pop stars, like Katy Perry, who somehow get off easier.) Still, what she lacks in technique she’s always tried to make up for with earnestness. Madonna works hard to sell a song, and the torch-y “Rain” is a fine example. Vocalists will never rave about her phrasing, but at least Madonna sings like she believes in every word.
27. Dress You Up (1985)
Madonna opened her very first concert tour, The Virgin Tour, with this ditty once deemed so provocative that it was ranked on the “Filthy Fifteen,” a list the Parents Music Resource Center compiled while advocating for album advisory stickers, alongside songs by Black Sabbath and Motley Crue. Its crime: Madonna wants to dress her man up in velvet kisses, a gesture that sounds pretty G-rated now. That a peppy little pop song like this made Tipper Gore’s tongue wag is a reminder of how rebellious even Madonna’s less-tawdry tracks once sounded. (Also, a reminder that Tipper Gore needs to get out more.)
26. What It Feels Like For a Girl (2001)
Madonna’s covered plenty of ground about how women are treated in the world, but she’s rarely this unfiltered: “Strong inside but you don’t know it, good little girls they never show it.” She showed plenty of strength (more like aggression) by taking a meek grandma on a violent joyride in the music video, directed by then-husband Guy Ritchie and set to an almost vocal-less club remix. The ferocious fantasy about simmering, tamped-down resentment finally bursting free was banned before 9 p.m. on MTV.
25. American Life (2003)
Damn you, Dixie Chicks. If your anti-Bush remarks hadn’t inspired “patriotic” (air quotes) yahoos to start stomping CDs, Madonna might never have pulled her original music video for “American Life.” (Which was maybe the most un-Madonna like decision she’s ever made.) On its own, the sparse, jarring song sounds more like an extended prologue to its American values-challenging album. But it’s heard anew when accompanied by its intended mini-movie, which compares the blindly obedient pro-war groupthink and rah-rah rallying cries that preceded the invasion of Iraq to applauding at a fashion show. And Madonna’s silly rap about yoga, Pilates, and lattes is revealed as a darkly comedic take on privileged First World Problems.
24. Die Another Day (2002)
Madonna tends to polarize people, and “Die Another Day” might best represent that curious talent. When it was announced that Madonna would record a James Bond film theme, a groan went up – yet the song became a Top 10 hit around the world. It was nominated for a Golden Globe – and a Golden Raspberry. And it frequently ranks on critical lists of best-ever Bond themes – and lists of worst-ever Bond themes. But this, after all, is the key to Madonna’s success: she demands a reaction. Love her or hate her, just don’t be bored by her. That’s how she’s lived this long in a churn-and-burn industry.
23. Girl Gone Wild (2012)
The latest anti-Madonna screed is that she’s too old to make dance club bangers about breaking it down and getting it on. That criticism seems bizarre, like telling Bruce Springsteen he’s too old to rock about the blue-collar American experience, or telling Eminem he’s too old to rap about his crappy home life: this isn’t some thing they do, it’s who they are. As a song, “Girl Gone Wild” is incredibly infectious but disposable dance-pop about cutting loose after feeling clamped down for too long. But as a Madonna Moment, it’s more significant. Look back at her younger days writhing in a wedding dress, and Madonna’s scandalous, subversive assertions of female sexuality seem quaint by today’s standards. Guess what? In twenty years we’ll look back and wonder why it was deemed so crass that a newly divorced, fitter-than-most fifty-something would proclaim (gasp!) she’s not ready for spinsterhood yet.
22. Give it 2 Me (2008)
From its too-trendy production to a lead single (“4 Minutes” with Justin Timberlake) on which she sounds like her own featured guest, Hard Candy, recorded during the demise of her second marriage, was Madonna’s mid-life crisis album. You could make a drinking game out of all her references to fleeting time and warrior-like promises that she can take a licking and keep on ticking. But this Pharrell Williams-produced manifesto deserves a toast for sheer moxie and steely mettle. “They say a good thing never lasts, and that it has to fall. Those are the people who did not amount to much at all,” Madonna asserts. Then she brags that, “when the lights go down and there’s no one left, I can go on and on.” Madonna bravado at its best.
21. Live to Tell (1986)
With “Crazy for You,” Madonna proved she could nail a hit ballad: for teenage girls to slow dance to at prom. But “Live to Tell” broadened her appeal with adult audiences, offering a mature, melancholic song about bearing the burden of some enigmatic secret and coping with a painful past. It’s ambiguous enough to connect with anyone and be reinterpreted to different ends. (On her 2005 Confessions Tour she performed it as a Christ-like figure on a mirrored cross, as a solemn ode to AIDS-orphaned children.) Whatever you hear in “Live to Tell,” its secret is yours to keep.
20. Papa Don’t Preach (1986)
“Papa Don’t Preach” is a declaration of independence from the POV of a girl in a catch-22. Somewhere in the ‘50s-era fantasia within which her True Blue album operates, Madonna plays the part of an unwed pregnant girl in love with a bad boy. Should she keep the baby or not? Some finger-wagging pops will deem her a sinner either way. Coming from a crucifix-adorned singer named Madonna, it’s pretty clear that Papa (Italian for “Pope”) is a stand-in for any authority figure that tries to tell her what to do. Madonna’s decision: when in doubt, self-determine.
19. Bedtime Story (1995)
Madonna has always combined a commerce-friendly sensibility with an eye and ear for the experimental. She gets a lot of credit for the former, much less for the latter. But pop in ear buds and turn loud this gurgling trip-hop lullaby, in which Madonna coos nonsensical stream of (sub?) consciousness lyrics with the conviction of someone explaining how galaxies are formed. Though an epic club hit, “Bedtime Story” became her first single since “Holiday” to miss the Top 40 on mainstream charts. Time has been kind, though. The surreal $5 million music video, then the most expensive ever made, is now in the collection of NYC’s Museum of Modern Art.
18. Give Me All Your Luvin’ (2012)
Coca-Cola. McDonalds. Madonna. The woman has turned herself into a global brand, and the lead single from her album MDNA is basically an advertisement for – well, herself. (“L-U-V Madonna!” scream her sycophantic cheerleaders.) The only-OK surf-pop song is transformed by its slyly funny video, an extended promo for her super-hyped Super Bowl show. It features Madonna the Marketing Machine unabashedly asserting that she’s turned America’s annual beer-and-buffalo wings blowout into an event about a pop diva: faceless football players take bullets for her, bend over so she can dance on their backs, and throw down jerseys to roll out the red carpet. (That narcissism was justified. Her all-time most-watched halftime show drew more viewers than the game itself.) GMAYL is basically a Madonna commercial for a Madonna commercial, the kind of smirking self-plugging that her haters abhor and fans adore.
17. Open Your Heart (1986)
Hard to believe since she’s now criticized for being a fitness freak, but in her early career Madonna took ribbing for being a voluptuous gal. With “Open Your Heart,” she debuted a new look: toned and tawny, using assertive (rather than come-hither) dance moves with echoes of her professional ballet training. The close-cropped hair was a change too, and Madonna’s new tomboyish beauty is played to the hilt in the video for “Open Your Heart,” a gender role screw in which she’s a stripper who calls the shots, her voyeurs are drooling goons, and a young boy can’t decide whether he wants to be with her – or just be her.
16. Take a Bow (1994)
“Take a Bow” is Madonna’s longest-running number one hit, yet one of the few she’s never performed on tour. (Never short on dramatics, she’s clearly reserving it as some career-capping swan song.) It’s the apex of her mid-90s balladry, and Madonna sent its Spanish-themed music video to Evita director Alan Parker as a pseudo-audition tape, fulfilling her long-held dream to play Eva Peron. Whatever her diva reputation, Madonna’s never too proud to beg for the work she really wants.
15. Justify My Love (1990)
By 1990, Madonna could read the phone book on the radio and score a hit. Still, it’s surprising that this spoken-word series of sexual vignettes (which would still sound edgy on the dial today) was a successful single. Not surprising: that its black and white video, in which Madonna depicted taboo same-sex smooching, caused a national furor and became her first banned by MTV. (She went on Nightline to defend herself.) Even less surprising: she thought to release it as the first-ever video single, and made millions anyway.
14. Like a Virgin (1984)
A girl named for the Virgin Mary, fondling herself in a wedding dress? Madonna can manufacture controversy better than anyone, and she really started strong with her first number one hit. From the moment she humped the stage at the first MTV VMA, it was clear she was a force to be reckoned with. But she never, let’s be clear, sold sex: she sold herself, and sex just came with the package.
13. Hung Up (2005)
Critics love to wax on about her waning star power. So it’s worth a reminder that Madonna’s most successful worldwide single isn’t from the ‘80s, or even the ‘90s: it is 2005’s “Hung Up,” which earned a place in the Guinness Book of World Records for topping the charts in 41 countries. Somehow the song is a perfect people pleaser, hitting all the right notes in its music and marketing. “Hung Up” merged modern dance with an ABBA sample for a spot-on song, and Madonna adopted a signature style (disco diva-meets-bodacious ballet teacher) that was received as sexy and classy. With “Hung Up,” it became clear this dancing queen still owns the throne.
12. Lucky Star (1984)
Madonna’s first Top 5 hit was accompanied by a low-budget music video that was shocking in its simplicity: just a midriff-baring, NYC street girl with DIY style crawling toward the camera with fire in her eyes and something naughty on her mind. Thus was born the blueprint for the now-standard sex stare, with accompanying bumping and grinding, that every pop starlet has essentially been mimicking since. Madonna’s gold standard remains unmatched, if only because her assured gaze manages to connote both sexiness and strength.
11. Human Nature (1995)
Madonna was an unhappy camper after the prolific slut shaming that met her Erotica album and SEX book. (YouTube her infamous expletive-filled David Letterman appearance, where she hijacked his stage and horrified the censors. It’s the closest this control freak ever came to a public meltdown.) “Human Nature” was her official response-via-song, a deadly serious rebuke of her critics coupled with a tongue-in-cheek undoing of her hyper-sexualized image. Over a slow-burn hip hop beat, Madonna spits back that she was raked over coals for challenging sexual taboos and treated as a whipping girl by hypocritical prigs. (“Would it sound better if I were a man?” she wonders.) In the end, there’s one thing she won’t offer: an apology. “Absolutely no regrets,” she declares. A Madonna mantra if ever there was one.
10. Frozen (1998)
Madonna’s music video for “Frozen” marked one of her most dramatic reinventions: gone was the platinum blonde bombshell, and in her place was a raven-haired, Goth-glam club witch, covered in Sanskrit inking and twisting and writhing in the desert of Death Valley. (Get it? Even the hottest place on Earth can feel, amid melancholy strings connoting emotional distance, frozen.) The change in look accompanied a greater change in sound. This first single from the William Orbit-produced album Ray of Light is full of skittering percussion and lush electronic elements that were innovative for a radio single 15 years ago, and still make “Frozen” sound cool today.
9. Music (2000)
Madonna has always had confidence, but she strutted into the new millennium with bona fide swag. (And a cowboy hat on her head. Giddyup.) This crunchy electro exercise updates the simple sing-along approach of “Holiday” for the space age, wrapping a galactic assortment of squelching beats and squiggling synths around a pretty basic command to play the damn record, Mr. DJ. The number one hit is Madonna at one of her least affected, most effortless moments.
8. Into the Groove (1985)
Madonna’s not exactly a passive dance partner. In “Into the Groove,” beat for beat one of the sassiest, spunkiest dance tracks ever, she demands that her boy toy prove his love, get up on his feet, step to the beat, and touch her body to move in time. Why? Because, “now I know you’re mine.” According to the math of Madonna-land, dancing equals sex equals power, and this let’s-boogie invitation is a far cry from most purring, coquettish sex kittens of pop. (Cough, Britney.) Madonna is a lioness who wants a guy that can rival her roar on the dance floor. And, you know, elsewhere.
7. Material Girl (1985)
Hold on to your sequined shoulder pads. This chirpy tune embodies the Reagan era’s glamorization of excess and avarice, the perfect backdrop for the rise of a star with the unapologetic hunger of Madonna: that middle-class Michigan cheerleader who, in her first major TV appearance, told American Bandstand’s Dick Clark that her goal was “to rule the world.” Shallow? Maybe. Empty? No. Madonna playacts a yelping airhead in the song, Betty Boop gone American Psycho, but the video underscores its irony: she’s really a self-possessed starlet who wants real love and handpicked wildflowers from a nice guy in a pickup truck. Diamonds may be a girl’s best friend, but this 1980s anti-Marilyn can buy them for herself, thanks-very-much.
6. Erotica (1992)
The clank of chains, the scratch of vinyl and copious moans and groans. With “Erotica,” Madonna invited listeners to meet her dominatrix alter ego, Dita, and bump and grind to house beats straight out of a gritty NYC fetish club. Its music video (banned by MTV except for late-night play) and Madonna’s simultaneously released art-porn book, SEX, showed the pop star cavorting in dungeons with every combination of sexual partner and explicitly depicting (sometimes lampooning) every type of fantasy. No pop star of her fame has been this sexually transgressive before or since, and Madonna paid the price: the backlash was harsh. Rihanna sings about “S&M” like it’s a song about My Little Pony, but Madonna dishes on pain, pleasure, and power with the conviction of a whip crack.
5. Get Together (2006)
Outside the clubs, this glorious single from Confessions on a Dance Floor was little heard. Too bad, because it’s a gorgeous gem that shines like a strobe light, and like an older, wiser, world-weary sibling to “Lucky Star.” Many other songs are more iconic, but sonically there’s something about “Get Together” that captures the essence of Madonna’s music: melancholy but hopeful, determined to spin itself out of the lonely shadows and on to the dance floor, a transcendent, unifying place where anything is possible and “love at first sight” happens with every turn of the disco ball.
4. Ray of Light (1998)
Let’s just put it out there: if you checked out when Madonna “got spiritual,” you’ve missed most of her best music. Early individual singles hit harder, but as start-to-finish albums her newer stuff trumps. And this now mid-career song marked Madonna’s turning point from a singles-focused artist to a headier, more conceptual one. Flush with the glow of new motherhood and leaving behind the confrontational nature of her Erotica-era work, Madonna dropped “Ray of Light” as a tab of juicy EDM ecstasy, sounding more joyfully blissed-out than ever before. From a singer who traffics highly in self-exploration, “Ray of Light” is an especially euphoric (and yes, inspirational) anthem about the tail-wagging joy of coming home to a happier version of your self.
3. Express Yourself (1989)
You can’t declare a song an “empowerment anthem,” any more than you can give yourself a nickname: these things must happen on their own. That’s why Lady Gaga’s “Born This Way” sounds like a patronizing head-pat from a faux outsider, while Madonna’s “Express Yourself,” the superior hit to which it has infamously been compared, offers something to really feel proud about. Its Metropolis-inspired video, in which Madonna portrays a satisfaction-starved concubine who takes control of her own destiny (crotch-grabbing CEO style) can give any in-need-of-inspiration listener a pick-me-up without talking down. Madonna doesn’t treat the listener as a precious, wounded misfit in need of sanctimonious rescue. She says: you’re strong enough on your own, but just need a beat to thump your chest to.
2. Vogue (1990)
“Vogue” captures Madonna at her most commanding. It’s a unifying call-to-arms for self-actualization on the dance floor, covering her most familiar lyrical ground: life is sad and life is hard, so lose yourself in the music where we’re all beautiful superstars. It’s also her most accomplished example of bringing underground art above ground; “vogue” dance was a hallmark of the (largely, black and Latino) ‘90s gay clubs, where its celebration of the Glamour that Lives Within connected with marginalized people. Madonna has occasionally been accused of cultural re-appropriation for taking vogue mainstream, but she never obfuscated or demeaned its roots. (Unlike say, Beyonce, who swiped the J-Setting dance style of “Single Ladies” from gay clubs, made the queer element invisible, and set it to a tune about heteronormative matrimony.) Even at an especially homophobic time, Madonna’s gay dancers were shown as front, center, and fabulous, striking a pose alongside the most famous woman on Earth.
1. Like a Prayer (1989)
Sex, controversy and nose thumbing at Catholicism (before it became an easy target): “Like a Prayer” contains the holy trinity of what makes Madonna – well, Madonna. She was nearly crucified for racy double entendres comparing romantic love to religious ecstasy, and a scandal-baiting video in which she smooches a black saint before angrily dancing in a field of burning crosses. (“Persecute this, patriarchy!”) Responding to boycotts, Pepsi infamously pulled a commercial featuring Madonna and the song. She kept her $5 million fee, but had earned something new, too: credibility as an artist who could turn pop music into cultural conversations. Three decades into her career, she still has us talking.
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