Madonna: A Highlight Reel of the Icon’s Most Memorable Eras in Style

A fidgeting, grinning 25 year-old girl batted her eyes across the crowd of American Bandstand, amid claps, shrieks and whistles. Her blonde-streaked hair was teased to one side and partially pinned to the back, and a black cropped t-shirt draped cooly off of one shoulder. She leaned into a microphone and declared to Dick Clark that her professional dreams were “to rule the world.” The girl’s name was Madonna.

It was 1984 and, having been signed to Sire Records only two years prior, with but one album on store shelves, it was a brazen statement to make. But, more than three decades later, she has exceeded 64 million record sales, won eight Grammy and two Golden Globe awards, and become the highest-grossing solo touring artist of all time. The Recording Industry Association of America named her the best-selling female rock artist of the 20th century.

She has sparked conversations about degradation, feminism, homophobia, misogyny, self-belief and sexuality, ever-challenging the status quo. She has spawned critics and imitators, and has been verbally assassinated and celebrated in equal measure. The world has been entertained, influenced, seduced, shocked and soothed by her. Love her or not, she has kept us on our toes—making us dance and keeping us guessing while refusing to ever be forgotten.

And she has done it all in style—through the commissioning of countless wardrobe designers, stylists, videographers and directors, and the experimentation of a vast range of hairstyles, eras and subcultures.

Ahead are three glamorous stories she brought to life along the way.

“Papa Don’t Preach”: The Complexities of Young Love, Rebellion and Self-Belief

The second single to be released from her third album, “True Blue,” it became Madonna’s fourth No. 1 song in the United States. The newlywed wife to actor Sean Penn at the time, she dedicated the entire album to him, declaring that he was “the coolest guy in the universe.”

This era was born in June of 1986, and solidified Madonna’s striking departure from the club-going image her fans had spent the previous three years obsessively emanating. She tossed them a curveball by discarding the lace, rosaries, ripped tights and layered accessories, reinventing herself as a more refined version of her trademark blend of button-pushing intelligence, irony, playfulness, rebellion and sex appeal—an edgier remix of classic Hollywood glamour. Her streaked blonde hair was cropped and bleached to platinum, reminiscent of Marilyn Monroe’s, and she revealed a tighter, sleeker and more toned muscular structure.

The song’s lyrics were rather controversial for the 1980s, and compelled women’s organizations to criticize the singer for romanticizing teenage pregnancy. Shortly after the song began blasting across radio airwaves, a spokesperson for Planned Parenthood told The New York Times, “The message is that getting pregnant is cool and having the baby is the right thing and a good thing and don’t listen to your parents, the school, anybody who tells you otherwise…” But, despite protests, the masses could not turn it off. The song inspired a swarm of gossip, mockery and even a lawsuit. But most significantly? Lots and lots of airplay. Also unwavering support from MTV, turning the controversial tune into a summer anthem.

Directed by James Foley, the music video for the track opened up with an interesting montage of New York City— the skyline, the Statue of Liberty and various urban characters, from street dancers to a flock of ravenous gulls to kids playing basketball. The first shot of Madonna, who played a strong-willed teenager who was raised in the working class borough of Staten Island, zoomed in on her feet as she walked through her neighborhood. The camera then glided up her body and revealed her casual dress of belted jeans and a striped shirt, soft nude makeup framing her penetrating gaze, and a black leather jacket draped over one shoulder.

Short clips of old home movies and flashbacks of the character as a child were immediately woven into the storyline, revealing the enduring bond she had with her father. Her boyfriend, the quintessential bad boy charmer, was played by blue-eyed actor Alex McArthur. When he entered the story, the two characters exchanged amorous glances, making it clear that they had created a world where the two of them existed most of all. Those scenes were juxtaposed with climactic shots of her dancing and singing solo in a darkened studio, dressed in a black bustier and a dance leotard, and appearing far more glamorous than in the previous scenes—her flawless ivory skin appearing almost ethereal, yet creating a soft backdrop for her bold red lips and strong eyebrows.

As the narrative progressed, Madonna was shown leaning against a fence railing alongside her girlfriends (one of whom is played by her real-life best friend Debi Mazar), wearing tight black jeans and a black t-shirt with “Italians Do It Better” printed in white lettering. Her friends seemed disapproving of her boyfriend’s questionable reputation, but it was clear that Madonna was staunchly undeterred, charging forward alone—conveying that she was willing to move forward without their support in order to protect what she believed in most of all.

The tension escalated when Madonna discovered she was pregnant, and a series of shots conveyed the internal wrestling and struggle of facing such an irreversible life change, while also pining for her father’s approval. There were offerings of emotional complexity and contrast—angst and self-composure, innocence and rebellion, vulnerability and strength—and all were conveyed through the dissimilarity between her appearance in the neighborhood street scenes and the glamorous shots of her dancing. The video concluded with her father accepting her pregnancy—reaching for her hand as she sat demurely in her bedroom.

Controversial as it may have been, and as much of a departure as it was image-wise, the video made history and solidified Madonna as not only a dominator of music charts, a global sex symbol and popular culture icon, but also a gutsy, unapologetic trailblazer who was not only unafraid of change, but also gave volume to the conversation topics others only spoke in a whisper. It won her Best Female Video at the 1987 MTV VMAs.

“Take a Bow”: The Entrenching Drama of Unrequited Love

For her sixth studio album, “Bedtime Stories,” Madonna softened her artistic delivery on the other side of the more dark and provocative “Erotica,” which coincided with the shocking release of her book, “Sex,” which was slaughtered by her critics. Though she claims its content was birthed from an organic evolution, as opposed to a contrived attempt to restore favoritism with the masses, “Bedtime Stories” was effervescent with soul-searching introspection and vulnerability; she lightened her hair as well as her persona. The album’s lyrics were romantically autobiographical, and its delivery was blanketed in sophistication. During an interview with MTV for the record’s promotion, Madonna was asked how she was able to determine when a song was finished. She said, “When my toes start to tingle. When I’m smiling. I can’t describe it. It’s like asking a painter, ‘How do you know when your painting is finished?’ It’s when it says what you want it to say.”

For much of the album’s recording, dripping with lullaby-esque melodies and oozing with urban influences, Madonna was secretly dating Tupac Shakur, who she collaborated with on an unreleased version of the album’s track, “I’d Rather Be Your Lover.”

But her co-creators, record executives and listeners all agreed: “Take a Bow” was a standout. Co-written and co-produced with Babyface, as well as backed by his harmonies, this mid-tempo ballad was supported by a full orchestra. The feel of it was cinematic, poetic and soulful, somewhat like opera meeting R&B, and it would be the record’s second single release. Radio adored it. It reached the No. 1 spot and lingered in the top positions of the Billboard Hot 100 for seven straight weeks—longer than any of her previous singles.

The music video, styled by legendary fashion journalist and editor Lori Goldstein, was a major production, and was filmed in Ronda, Spain—an ancient town set way up high in the mountains in the country’s scenic southern region. Madonna confessed that, when she and her crew arrived in the town for filming, she checked into a small boutique hotel but quickly had to relocate; fans were surrounding its quarters, shouting her name, and some were attempting to climb its walls for a chance to catch a glimpse of her in a private moment.

Madonna conceptualized the video with its director, Michael Haussman, who had developed a curiosity and fascination for matadors. The two agreed that the bullfighting narrative served as a metaphor for the emotionally abusive, obsessive and unpredictable nature of the love affair portrayed in the song, as well as the tragic brutality of accepting when affections would always be unrequited. When asked why a Spanish motif often surfaced in her art and style, Madonna said, “I was Spanish in another life.”

The video opened up with Madonna draped over a television set, her famous bullfighting lover on display (played Emilio Muñoz), as her fingertips slowly stroked the screen with sorrow and longing. Shot entirely in sepia tone, much of the storyline unraveled inside of a 500 year-old house, meant to be portrayed as a hotel room, where Madonna shifted between isolation and longing for her lover —rolling around on a bed in lingerie in one steamy scene, to being seduced and then discarded by him—sinking into a cornered wall while drenched in jewels, curling into herself, appearing desperate and ravaged, lipstick smeared across her cheek. It showed her lover’s footsteps moving across broken glass as he abandoned her. In between, there were shots of his bullfighting performances with her watching him from the crowd, along with offerings of Catholic imagery.

The main outfit was a low-cut, corseted piece from John Galliano’s 1994 fall fashion show, reminiscent of the 1940s, which was paired with long, black gloves. Madonna said this ensemble was chosen because the restrictive aspect of its design fit the emotional theme of the song and video. It was accompanied by tragically romantic and theatrical makeup that offset her platinum blonde hair: dark winged eyeliner, plush eyelashes, porcelain skin and deep cherry lips.

In one of the more memorable scenes, she was shown running along a stone wall while dressed in a long, dark and shimmering backless dress, also designed by John Galliano. She moved her hand along the wall’s grooves in a synergistically dejected and sensual fashion. Her nails were trimmed short and polished with a vampy red shade—almost similar to the color of dried blood.

Fans were infected by the song’s melodic hooks, and became entrenched in the video’s drama. It won Best Female Video at the 1995 MTV VMAs, and Goldstein was honored a VH1 Fashion and Media award for styling it.

“Hung Up”: Humankind Is a Dance Party and Everybody Is Invited

The “Confessions” Era | Photo By Joey McCoy ©2006

Times had changed for the inexperienced girl who once told Clark she wanted to rule the world. Now considered by all as an incredibly multi-faceted entertainment icon, as well as having become a mother, a part of her longed to revisit her roots—where unabashed freedom found sweat-drenched bodies gyrating into the wee hours of the night. Alas, her tenth album, “Confessions on a Dance Floor,” was given life and released in the fall of 2005. In an interview for promotion of it, when asked what inspired its concept and feel, she said, “I feel like dancing.”

“Hung Up,” with its catchy lyrical hooks, dance-pop-meets-disco personality and ticking clock, featured a sample of ABBA’s “Gimme! Gimme! Gimme! (A Man After Midnight),” and was throbbing, celebratory, liberating and fun. Madonna received glowing permission from the group to sample their song, and “Hung Up” was an obvious first single. It received instant praise from listeners.

For its accompanying video, shot less than three months after Madonna suffered eight broken ribs from a horse accident on her 47th birthday, she held a specific vision in mind. Inspired by “Saturday Night Fever,” she said it was her intention for the video to be “a tribute to John Travolta and that whole era.” She also admitted to having drawn inspiration from Jamie Lee Curtis in “Perfect” and Olivia Newton John in “Grease.”

Directed by Johan Renck, the mini-movie began with Madonna walking into a rehearsal studio, lugging a large boombox. She stripped away her green tracksuit, revealing a hot pink leotard, a purple sequined belt, flesh-colored dance tights and strappy heels—her strawberry blonde hair in a youthful Farrah Fawcett style. Her makeup was radiant, showcasing glossy nude-peach lips and flushed cheeks. Viewers would be most astonished by her ballet-esque physique: firmer, leaner, tighter and more sculpted than ever.

She shimmied, gyrated and high-kicked around the room, gliding along a ballet bar and mirrored wall. It quickly became known that this scene served as the backbone for a reel of mini-narratives which explored a variety of subcultures within the world of dance. There were teenagers in playful competition with each other in a Los Angeles neighborhood, London Underground dancers, servers performing a choreographed sequence in a Chinese restaurant and others scaling and leaping across buildings in France—just to name a few. A contortionist also made a daring contribution. The boombox was a constant in every scene, tying all of the wildly different forms of movement into a unified expression and giving it an omnipresent feel.

The video’s stylist, Arianna Phillips, proudly admitted that a majority of the pieces Madonna wore were authentically from the 1970s. In one of the scenes, the singer walked down a street in London at night, wearing a hooded black leather jacket (which was revealed to have been purchased from a thrift store somewhere in the middle of nowhere), paired with Prada jeans and a vintage green sequined belt. She then arrived to a club, which served as the the story’s climax, where she stripped away the jacket and revealed a green leotard, also vintage—and appearing as though she had been plucked from the set of “Saturday Night Fever.”

She spun and twisted seductively alongside a few dancers, encircled by a crowd of others breakdancing around her. It was a celebration without restraint. The club scene was offset by another surreal, dream-like setting where Madonna again wore the hot pink dance leotard, this time coupled with a sheer, flowy and cropped pink top, while writhing around on a shiny black stage, alone—a disco ball effect lighting up her flesh in interesting, monochromatic patterns reminiscent of hot, sweaty nights spent at New York City’s Danceteria in her early days of semi-obscurity.

Aside from the video being nominated for five MTV VMA awards in 2006, the song was so memorable, it landed in the No. 1 spot of charts in 41 countries. Also the Guinness Book of World Records. 

Lacey Johnson

Madam Wonder: Founding Editor

Lacey Johnson is an award-winning editor, essayist and journalist who earned her degree from Belmont University in 2011. She has worked with a broad range of celebrities and entrepreneurs — including the likes of Betsey Johnson, Deepak Chopra, Shark Tank's Daymond John and Olympic Gold Medalist Shawn Johnson. She is editor-in-chief for The Connect magazine, and her work can be read in a variety of print and digital media sources including Cosmopolitan, Marie Claire, Woman’s Day, Mirabella, PopSugar, and others. With a deep intrigue for human beings, and fiery passion for smacking her readers in the face with the truth, she writes and reports boldly about topics that challenge the status quo — in the realms of love and relationships, popular culture, travel, spirituality, women’s issues and the nuances of a fulfilling life. She is also deep in the process of co-authoring her first book, which is a gutsy exploration of the illusions of fame, power and success, told through narratives involving some of the people the world most idolizes.

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