Madonna’s 5 Most Memorable Videos 

Like a fine chef, Madonna’s career was always as much about the presentation as the product. From her earliest blend of Christian iconography and thrift store fashion (echoing punk contemporaries such as Pleasant Gehrman and Texacala Jones) through her various disposable guises, she understood that pop music was a form of fashion and thus required constant reinvention to stay fresh and relevant. It’s no coincidence she was essentially birthed by a brand-new national music video channel.

Videos by American Songwriter

Indeed, her stature began to slip not just when hip-hop and boy bands began pushing into pop, but because the video’s cachet began fading in the mid-to-late ‘nineties’90s, and by their conclusion, videos were little more than an afterthought for labels and a rather expensive one given their more limited impact on the charts.

This makes Madonna’s video oeuvre not only as vital as the music they contain, but essential evidence in understanding her lasting influence, and an irreducible part of her artistic legacy. Unfortunately, that facet is bound to be overlooked as videos become as unfamiliar to successive generations as an artist whose music isn’t available on Apple, Spotify, or Amazon.

1. Material Girl (1984, directed by Mary Lambert)

This iconic video achieves much of its power by paying homage to a classic Marilyn Monroe scene from Gentlemen Prefer Blondes, however, it’s a film-within-a-film, and the framing suggests that’s just a role. In the beginning, she sits in her dressing room unimpressed by an admirer’s gift of a diamond necklace, offering it to her friend. In the end, the big-shot producer buys a beat-up truck to appear more authentic and ends up making out with her in the cab while it rains. Apparently, the key to success is understanding everything’s a pose.

Interestingly, she met her future husband Sean Penn on the set because his former personal assistant, Meegan Lee Ochs, daughter of folk singer Phil Ochs, was working the shoot and he first saw her in full regalia, in a case of life imitating art.  

2. Like A Prayer (1989, directed by Mary Lambert)

Madonna works again with Lambert and the idea of artifice to provide a happy ending that the video’s narrative can’t provide, and for the first time but not the last, Madonna pushes public “standards” with the video’s interracial kiss. It was a bold play for the freshly 30-year-old artist, newly divorced from Penn and in the wake of two failed movies—Shanghai Surprise & Who’s That Girl.

The video was essentially backed by Pepsi, part of a $5 million endorsement deal. The track was previewed with a 30-second commercial clip—a preview of a commercial—on that year’s Grammys, before premiering 10 days later, during an episode of The Cosby Show.

But Madonna pulled a bait-and-switch, replacing what Pepsi thought was a happy video about an 8-year-old Madonna birthday called “Make a Wish” with a story of a black man jailed for a crime committed by a white man. It only avoids the bummer ending implied by our shared reality by turning the jailed and the bereft gospel chorus begging for justice into a theatrical performance complete with bows and a curtain. 

Pepsi canceled their deal, and Madonna basked in the controversy, cracking, “I made a video and it made some people mad. Drank some Pepsi and called it a day.” Who’s a Material Girl?


3. Vogue (1990, directed by David Fincher)

This song was ubiquitous and became her biggest international hit, going to No. 1 in over thirty countries. It tapped into a gay dance craze involving flamboyant hand gestures and frozen poses making overt the affected presentation. Madonna had recently paired up with Warren Beatty, then 53, appearing together in the movie Dick Tracy, and the video’s wardrobe leaned heavily into the ‘20s and ‘30s era style, particularly their dapper three-piece suits and Art Deco backgrounds.  

Before he went Hollywood, Fincher did commercials and videos. Many of the video’s compositions correspond to famous shots from the ‘40s by fashion photographer Horst P. Horst, who objected to their recreation without his permission. There was additional controversy because it’s possible to make out a nipple at one point in the camera closeups of Madonna caressing her sheer-laced breasts. She refused to cut it from the video and MTV relented.

4. Bedtime Story (1995, directed by Mark Romanek)

One of the most important things a pop artist can do is use their platform to expose and popularize other artists’ thoughts and ideas. Madonna in particular took this opportunity seriously and used “Bedtime Story” as a canvas for several female surrealist painters, notably Leonora Carrington, Remedios Varos, and Frida Kahlo. So if you don’t particularly understand the video, that’s fine, it’s not a traditional narrative so much as a sort of visual poem/dream state deeply informed by surrealism and cubism as well as Egyptian, Sufi, and mystical symbology. 

The video was the most expensive ever made at the time, costing over $5 million dollars. Thanks to its highly aesthetic nature it’s been displayed in art museums across the world, including New York’s Museum of Modern Art (MoMA). Critics have noted elements of androgyny and masquerade, obviously popular subjects in her oeuvre. 

5. Ray of Light (1998, directed by Jonas Akerlund)

Madonna reached out to Akerlund after filming her “Frozen” video with Chris Cunningham in the Mojave Desert and delivers something enjoyably off-beat and authentic compared to that ponderous self-serious video allegory. It pays homage to Godfrey Reggio’s 1982 cult-classic Koyaanisqatsi, a Hopi Indian word meaning life out of balance using the same sped-up, cross-cut, time-lapse photographic style (even a hamster wheel) to evoke our careening life. Dressed in denim Madonna dances energetically over careening highways and landscapes before landing in a crowded dance club clad in a simple white t-shirt, the universal and global reduced to a sweaty outpouring. Refreshingly low-concept and unpretentious.

Photo by Dave Hogan/Hulton Archive/Getty Images

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