Slant Magazine: 25 Greatest Videos

Posted October 6, 20222 yr

Madonna’s 25 Greatest Music Videos
October 6, 2022 | by Slant Staff

Madonna helped pioneer the music video as not just an essential marketing tool, but a legitimate mode of artistic expression.

When Sire Records sent the music video for Madonna’s first single, “Everybody,” to dance clubs 40 years ago, no one could have predicted that the drab, $1,500 performance clip, filmed at New York’s Paradise Garage, would herald one of the most influential video artists of all time. Dressed in khaki capris, a gray plaid shirt, and a brown, oversized vest, the singer appeared unremarkable and underlit—she hadn’t yet found her Joseph von Sternberg—but she oozed charisma, and her command of both the stage and the camera was palpable.

Madonna would famously go on to pioneer the music video as not just an essential marketing tool, but a legitimate mode of artistic expression alongside the likes of Michael Jackson in the ‘80s. She fearlessly pushed the creative and technological boundaries of the medium throughout the ‘90s in ways few of her superstar peers did, and has continued to produce iconic visuals well into the 21st century.

Videos also provided Madonna a way to flex her oft-maligned acting chops, without which many of these mini-movies would not just fall flat, but collapse under the weight of their narrative or conceptual ambitions. She convincingly embodies characters as multivaried as a pregnant teen (“Papa Don’t Preach”), a battered wife (“Oh Father”), a goth siren (“Frozen”), a stripper with a heart of gold (“Open Your Heart”), and, to quote our review below, the high priestess of a futuristic wage-slave community who celebrates the power of her repressed mechanism via self-love (“Express Yourself”), to name just a few.

The 25 videos on this list span 35 years, from Madonna’s breakthrough clip, 1984’s “Borderline,” to one of the visuals from her most recent album, 2019’s Madame X. Not surprisingly, it’s the videos from the Queen of Pop’s imperial phase that dominate: Nearly every video she released between 1986 and 1993, save for a few throwaway soundtrack tie-ins, is present and accounted for here.

For Madonna, videos were more than simply a method of promotion; they served as a platform for her political and social messages, and a means to pay homage to her influences. Part of her legacy may be forever linking an artist’s image and visual interpretation to their music itself, and she’s done it better and more consistently than practically anyone else. Sal Cinquemani

25. “Dark Ballet” (Director: Emmanuel Adjei)

The audacious, Tchaikovsky-sampling “Dark Ballet,” from Madame X, received an equally bold video starring Mykki Blanco as Joan of Arc. The clip is a tumultuously powerful, if unsubtle, depiction of resistance to transphobia and homophobia, and Madonna appears only briefly, leaving Blanco’s full-force dynamism to track each and every fluctuation in the style and tone of the song. Religious imagery is far from new in the Madonna universe, but here it’s deployed in service of an intersectional perspective, one that keeps the singer’s videography forward-thinking even when she’s treading familiar thematic ground. Four decades into her career, Madonna continues to find new ways to stay ahead of the curve, signal-boosting Blanco’s urgent, excoriating pleas for humanity through a lens that’s both timeless and historic. Eric Mason

24. “Girl Gone Wild” (Director: Mert & Marcus)

As Madonna has aged, she has, frustratingly, become a caricature of her past incarnations, a quality tempered somewhat by both her obvious self-awareness and her critics’ stunning lack thereof. Sometimes she hits the mark, as she does so brazenly in 2012’s mesmerizingly campy “Girl Gone Wild.” Made up like a Russ Meyer-style super vixen, Madonna, then 53, puts her 33-year-old self to shame, performing gravity-defying calisthenics—and whatever it is she’s doing with that giant exhaust hose—while wearing f***-me pumps. The video is an empty-calorie re-interpretation of the singer’s infamous “sex” period, mixing androgyny, religious imagery, voguing, and group—shall we say—choreography in a sleek, black-and-white package seemingly designed to be played on a loop at every gay bar in the world until the end times. Cinquemani

23. “Borderline” (Director: Mary Lambert)

It’s entirely possible that part of the reason so many people took umbrage at Madonna’s unapologetic sexuality is because, at the dawn of her career, she had already given pop music some of its most winsome moments ever. The music video for “Borderline”—her first collaboration with Mary Lambert, who would go on to direct five Madonna videos, four of which appear on this list—establishes the singer’s boho chic look as well as her playful, urban cred. And really, that’s sort of the whole point. The clip, which follows a burgeoning starlet who’s torn between her pre-fame lover and the photographer who discovers her, is as simple and direct as the song’s message: Be with me and you’re going to have a really good time. Eric Henderson

22. “American Life (Director’s Cut)” (Director: Jonas Akerlund)

Filmed in the weeks leading up to the U.S. invasion of Iraq in 2003, “American Life” may have been the first time in Madonna’s career where she voluntarily self-censored her work. In the original version, the artist and a band of unconventional beauties storm a fashion show that includes models dressed in military garb and gas masks, Middle Eastern children modestly strutting their stuff, and limbless soldiers trailing blood down the catwalk. Madonna and her radical fashionistas pummel the paparazzi with water from an industrial-size hose while the audience hoots and hollers at the spectacle. The backlash Madonna might have suffered at the time likely would have made the proverbial whipping she endured for her Sex book seem like harmless roleplay, but the video turned an awkward, self-aggrandizing song about privilege into a startling comment on the obscenity of war and materialism—one that would have undoubtedly been looked back on as brave. Cinquemani

21. “Deeper and Deeper” (Director: Bobby Woods)

A tribute to the films Andy Warhol produced for Paul Morrissey, “Deeper and Deeper” features a smorgasbord of contemporary cameos (Debi Mazar, Sofia Coppola, ChiChi LaRue) and Morrissey alums (Udo Kier, Holly Woodlawn) as patrons of a bustling Hollywood nightclub. Madonna, who portrays Warhol protégé Edie Sedgwick and arrives with balloons in hand, is drawn to the basement of the club, where Kier has corralled his misfit minions. The video is weird, dark, and alluring, with themes of innocence lost and the occult butting up against overt camp (a stand-in for Joe Dallesandro, another Morrissey alum, performs squats in his skivvies while the singer and her friends nibble on bananas). When a barfly begins to pop her balloons, she snatches them and scurries away—but not before the über-creepy Kier cuts them loose in the parking lot. Cinquemani

20. “La Isla Bonita” (Director: Mary Lambert)

“I was Spanish in another life,” Madonna once cheekily declared. The artist’s belief, however serious, that her preoccupation with Latin culture is rooted in a sort of spiritual duality dates as far back as the video for 1986’s “La Isla Bonita.” In the clip, Madonna, wearing a simple white tank dress, peers longingly down from the austere confines of her apartment at the street party below. Later, she kneels before a makeshift altar of photos of indigenous-looking women, perhaps attempting to summon their strength. The washed-out watercolor palette is juxtaposed with rich, candle-lit scenes of Madonna’s alter ego in a red Andalusian-style dress, representing a form of spiritual and sexual freedom (as she lays on the floor, her hands inevitably find their way between her legs). Eventually, the alter ego (or is it the “real” Madonna?) steps out, leaving her sadness behind, to dance through the streets—a perfect summation of the power of music, dance, and performance. Cinquemani

19. “Cherish” (Director: Herb Ritts)

“Cherish” is notable for not just being the late photographer Herb Ritts’s first foray into music videos, but for its surprisingly lighthearted, family-friendly tone following the provocative “Like a Prayer” and “Express Yourself.” Despite three strapping mermen cavorting nearby in the ocean, captured sensually by Ritts’s lens, Madonna is content to frolic in the sand with a young merboy. As in “Open Your Heart,” the singer seems drawn less to carnal temptation than to the innocence that the boy represents. All of the videos from Like a Prayer serve as mini-parables, and though the frothy “Cherish” might, at first blush, seem like an exception, the final shot reveals the boy, having grown legs, gazing forlornly down at Madonna, who lays on the wet sand helplessly, the lower half of her body just out of frame. Like the Little Mermaid who gives up her voice for a pair of legs and a human soul, Madonna appears to sacrifice hers for the boy’s freedom. Cinquemani

18. “Bad Girl” (Director: David Fincher)

The fourth and (sadly) final collaboration between Madonna and director David Fincher, the star-studded “Bad Girl” draws on more contemporary film references—the 1977 cautionary tale (some might say $l*t-shaming) Looking for Mr. Goodbar and Wim Wenders’s 1987 film Wings of Desire—than their previous videos. Madonna plays Louise Oriole, a bombshell business exec who smokes, drinks, and f***s her way into a body bag. Filled with clever visual tricks—check out that flawless blacktop/bartop dissolve—“Bad Girl” previewed the icy, neo-noir aesthetic that would define Fincher’s filmography in subsequent years. Not a single frame, prop, or character is without intention here, and Christopher Walken presides over the proceedings as—take your pick—the Grim Reaper, Louise’s guardian angel, or a proxy for Fincher himself. The latter interpretation is bolstered by the final shot, of Walken and Madonna sitting side by side on a crane—co-directors of the scene unfolding below. Cinquemani

17. “I Want You” (Director: Earle Sebastian)

The video for Madonna and Massive Attack’s cover of Marvin Gaye’s “I Want You” takes place in a civil rights-era hotel room where a disheveled Madonna paces, literally wringing her hands as she waits for the telephone to ring. In a tactile, wordless performance that might be the most convincing evidence yet that Madonna the actress was born a century too late, she removes her fake eyelashes, listlessly tidies up the room, and rummages through the dresser, frantically trying on clothes to pass the time. There are hints in her quietly escalating desperation that the fix she’s waiting for may be more than that of a lover. But like all things Madonna, the video’s ambiguities are far less important than her final message of self-empowerment: When the call she’s been waiting for finally comes, she hangs up the receiver. Cinquemani

16. “Secret” (Director: Melodie McDaniel)

The videos from Madonna’s R&B-influenced Bedtime Stories display an ostensible need on the artist’s part to explore her own conflict as a cultural riddle. In “Secret,” Madonna plays a white chanteuse in Harlem, but that she keeps a relative distance between herself and the mostly Black and Latino people in the video suggests an earnest belief that a white woman’s intimacy with those from an “other” culture is one that must be carefully earned. As in “I Want You,” her “secret” is initially ambiguous, with subtle references that suggest the scourge of addiction in inner-city communities: Throughout, characters are seen covering or nervously stroking their arms, and Madonna’s “cleansing” ritual could be interpreted less as a spiritual purification than a physical detox. But the secret (or one of them) is ultimately revealed to be a mixed-race child—a transparent justification for her presence in this particular milieu when, given her soul-sister bona fides, none is needed. Cinquemani

15. “Erotica” (Director: Fabien Baron)

Whereas in “Justify My Love” there was just a hint that at least some part of Madonna felt the shame of guilt, “Erotica” finds Madonna immersed fully into the role-playing kink of it all. If the earlier song was an admission, this was the mission statement, and no one has ever looked less like they’re playing games when it comes to, well, wanting to play games. “My name is Dita,” she purrs at the start of the song, a reference to L’Atalante star Dita Parlo, who very notably feels herself up near that film’s climax. Madonna’s version, on the other hand, sports a gold tooth, hitchhikes in the nude, and dominates entirely willing subs, all filmed in grindhouse-ready 8mm by Fabian Baron during the shoot for her accompanying Sex tome. And somehow, she was just getting warmed up. Henderson

14. “Rain” (Director: Mark Romanek)

With the video for the fluid-filled “Rain,” already Erotica’s least pugnacious moment, Madonna launched the great post-Sex rebuilding phase of her career. Not exactly out of penitence, one suspects, but with an eye toward widening the scope of her appeal back to its earlier levels, lest she burn out in a blaze of sexual glory. Adopting a more muted persona, swapping blond for brunette in a Louise Brooks-esque bob, Madonna recruited visionary director Mark Romanek to approximate the steely blue vibe of the song’s titular storm. It’s the exact opposite of threatening but no less sensation-driven than the videos that led up to it. Henderson

13. “Bedtime Story” (Director: Mark Romanek)

One of the most expensive videos ever made, “Bedtime Story” is a flurry of uncanny imagery steeped in contemporary CGI technology but rooted in surrealist tradition, from the works of Leonora Carrington and Frida Kahlo to Sergei Parajanov’s The Color of Pomegranates. Much like the undulating petals of the digital flower that blossoms around Madonna’s head at the start of the video, “Bedtime Story” offers innumerable images to pluck and peel back, revealing not only reference points, but also an embrace of the spiritual transcendence of the nonverbal depicted in the lyrics, written by Björk. Through images of mouths for eyes, supernatural levitation, and symbolism from Eastern religions, Madonna and director Mark Romanek construct a monument to the unexplainable sway of human connection. Mason

12. “Papa Don’t Preach” (Director: James Foley)

With her pixie blond cut and 1950s-style duds, “Papa Don’t Preach” marked the first time that Madonna radically changed her image, setting a trend not only for her career, but for the pop landscape at large. In her markedly boyish, gamine styling, which contrasts sharply with the glamorous extradiegetic Madonna of “Material Girl,” she’s removed from the celebrity stratosphere and returned to the streets of New York, where the story in the song’s lyrics is played out beat for beat. In addition to igniting controversy over freedom of choice and teen pregnancy, Madonna continued to revolutionize the music video form by expanding its capacity for narrative. Mason

11. “Like a Prayer” (Director: Mary Lambert)

Canceled multi-million-dollar Pepsi deal and uproar from both the left and right over burning crosses aside, the iconic video for 1989’s “Like a Prayer” tells a simple yet enduring morality tale: After witnessing a case of racial profiling, Madonna seeks refuge in a church, where she takes a power nap on a pew and dreams of locking lips with the sentient statute of a Black saint—who looks an awful lot like the man who, earlier in the clip, was falsely arrested for assaulting a white woman, who looks an awful lot like Madonna—after which she awakens with the wisdom and courage, to quote the Spike Lee film from the same year, to do the right thing. Madonna was either naïve or shameless enough to depict herself as a literal white savior, but while some critics at the time accused her of appropriating Black culture for less than holy purposes, her intent was clearly not to exploit but to expose. To wit, the church is revealed to be a prison, and the prison is in turn revealed to be a theater. The moral of the story: All the world’s a stage, and some things never change. Cinquemani

10. “Ray of Light” (Director: Jonas Akerlund)

One of Madonna’s least conceptually complicated videos, “Ray of Light” finds the new mom gyrating before a backdrop of rapid-fire images inspired by Godfrey Reggio’s 1983 film Koyaanisqatsi (also a source of influence for Grace Jones’s 1981 video “Pull Up to the Bumper”). Both “Ray of Light” and its video served as a celebration of Madonna’s then-newfound spirituality and appreciation for life in the wake of the birth of her first daughter. “I feel like I just got home!” she wails throughout, but it’s the latter nighttime portion of the video—in which the singer teleports through a traffic tunnel and lands at the heart of a San Francisco dance floor—that truly feels like a homecoming. Cinquemani

9. “Human Nature” (Director: Jean-Baptiste Mondino)

A clapback at critics who accused Madonna of pushing the envelope too far, “Human Nature” is about as subtle as a slamming door. The clip finds the artist boxed in, chained up, and muzzled, but she has no trouble communicating her message. Sporting cornrows and surrounded by almost entirely non-white dancers, Madonna tip-toes dangerously close to equating her perceived persecution with the plight of racial discrimination, but as ever, it helps that she continually pokes fun at herself and her hyper-sexualized image. In contrast to “Justify My Love” and “Erotica,” the former of which was also directed by Jean-Baptiste Mondino, “Human Nature” feels like a Party City send-up of her Sex persona, with costumes that are decidedly latex rather than cold leather. It was the ultimate piss take of Madonna’s bondage period…until 2012’s “Girl Gone Wild.” Cinquemani

8. “Justify My Love” (Director: Jean-Baptiste Mondino)

“Justify My Love” advanced Madonna’s sexual gamesmanship beyond anything she’d attempted to that point, moving past double entendres and religious transgression into the realm of pure, aural porn. The steamy, chugging, extremely wet sound said all you needed to know whether Madonna intended to push the envelope further going into the ’90s. And it was even still somewhat (all right, entirely) overshadowed by its “too hot for MTV” music video, which puts Madonna’s hedonism in literal black-and-white relief. In the Jean-Baptiste Mondino-helmed clip, she careens through a hotel with a lascivious grimace on her face from one (bi-)sexual encounter to another, not unlike Shelly Duvall at the climax of The Shining, only swapping blood pouring from elevators with bodily fluids. In other words, one hell of a way to cap off both the first decade of her storied career and the so-called Reagan years. Henderson

7. “Material Girl” (Director: Mary Lambert)

The video for one of her signature hits sees Madonna deconstructing femininity, sexuality, and, of course, materialism in a postmodern fashion that set the stage for much of her career. “Material Girl” is an homage to Marilyn Monroe’s “Diamonds Are a Girl’s Best Friend” from the 1953 film Gentlemen Prefer Blondes, set to the crass ideals of the Reagan era. But Madonna’s character is savvier than Monroe’s Lorelei Lee, eliminating the other women from the original number and flexing her own feminine wiles. Of course, a self-parodying Madonna is only masquerading as a gold-digger; she simply wants some good old-fashioned love inside a pick-up truck. Cinquemani

6. “Hung Up” (Johan Renck)

While, superficially, the video for the rousing, ABBA-sampling “Hung Up” bears little connection to the song’s lyrics, it draws a parallel between yearning for a lover and anticipating a vibrant night out, making a case for dance as a form of connection that transcends distance and difference. Madonna, clad in a hot-pink leotard, pays tribute to Saturday Night Fever alone in a studio as the video’s diverse cast members display a more modern array of dance styles—including the then-popular krumping and parkour—eventually convening in a nightclub to play Dance Dance Revolution and join in their celebration of music with unfettered joy. Ultimately, “Hung Up” makes manifest a message from another Madonna dance anthem: “Music makes the people come together.” Mason

5. “Oh Father” (Director: David Fincher)

The death of Madonna’s mother reverberates throughout her discography, and the artist’s early confrontation with loss is put on powerful display in the cinematic video for 1989’s semi-autobiographical “Oh Father.” The dreamlike and disturbing clip, directed by David Fincher, takes its visual cues from Citizen Kane, casting an icy pallor over images excavated from Madonna’s memory, including a confrontation with her grieving father and the sewn-up lips of her mother’s corpse. Rather than demonizing her father, whose misplaced ire prompts him to rip his dead wife’s pearls from a young Madonna’s neck, the singer offers a lesson in ending cycles of abuse by confronting trauma directly. The final image of a young Madonna dancing over her mother’s grave feels like a reclaiming of her pain—one of many mission statements slyly written into her videography—and of turning the legacy of her loss into art. Mason

4. “Frozen” (Director: Chris Cunningham)

Just as she sought to imbue electronica with heart on 1998’s Ray of Light, Madonna lent director Chris Cunningham’s stark, icy visual style a sense of humanity—and reportedly reined in his penchant for special effects—in the first video from the album. As a siren lost in an unidentified desert landscape, Madonna morphs into a flock of ravens, floats in the air like a specter, dances with herself in triplicate, and summons a cosmic storm with the twirl of her Henna-covered hand. The overriding theme of “Frozen,” however, is self-imposed isolation, and the video’s simplicity keys into Madonna’s straightforward but resonant refrain: “You’re frozen when your heart’s not open.” But it’s another lyric—“You only see what your eyes want to see”—that highlights the clip’s inherent ambiguity: Its hypnotic effect is not unlike succumbing to one’s own psychological paralysis. Cinquemani

3. “Open Your Heart” (Director: Jean-Baptiste Mondino)

“Don’t try to run, I can keep up with you,” Madonna promises on “Open Your Heart,” and given the unflappable momentum of the track’s undulating bassline and the blithe directness of the singer’s basic argument, you don’t doubt her for a second. “Open Your Heart” is a major wrench in the argument that, at least in her first 15 or so years as a musical force, Madonna’s vinegar was more powerful than her sugar. The song’s video positions her as the most wholesome, kid-friendly peep show stripper you’ve ever seen. The ’80s may not have been a more innocent time, but it’s hard to imagine anyone getting away with dancing off into the sunset with a 12-year-old boy as Madonna does in the clip’s sun-kissed denouement. Henderson

2. “Express Yourself” (Director: David Fincher)

“Express Yourself” is the embodiment of queer chic, a bombastic masterpiece that heralds Madonna’s uncanny ability to use her consumer-driven image to code her feminist politics. Something this inspired by Fritz Lang’s Metropolis is not without theoretical implications. Here, Madonna plays the high priestess of a futuristic wage-slave community who celebrates the power of her repressed mechanism via self-love. The clip’s infinite metaphors are intricate and delirious without ever being pedantic. While Madonna looks for a way to vicariously penetrate the slave kingdom below her secret tower, sexual frustration begets physical aggression. Director David Fincher evokes the glamour and exoticism of male-on-male competition via the slave community’s constant flexing and cockfighting. Inside her postmodern living quarters, the five-foot-three Madonna towers above the crowd, slithers under her dining room table, and asserts her feminine wile. “Express Yourself” is as conceptually audacious as Metropolis because it celebrates both the power of the female sex and its ability to cripple the machine that dehumanizes it. Ed Gonzalez

1. “Vogue” (Director: David Fincher)

Look closely when that butler brushes off the bannister. Nope, no dust there; the finger pulls clean. Those who objected to Madonna’s co-opting two vibrant New York scenes—ball culture and the house underground—had every reason to cast any available aspersions once the music video for “Vogue” hit the airwaves. Directed with diamond-cut precision by David Fincher long before he became the fussiest of the A-list auteurs, the already plush song became a plummy fantasia of Old Hollywood luxury, and an actualization of the sort of glamour Paris Is Burning’s drag queens and dance-floor ninjas openly longed for. And it came with a steep price tag. “It makes no difference if you’re black or white,” goes the familiar refrain, but it’s unclear whether Madonna realized to what extent the clip’s flawless, monochromatic cinematography would underline the point. To some, the video (like New York’s ball scene) represented the ultimate democratization of beauty. To others, a presumptuously preemptive eradication of the racial question entirely. Henderson