1 of 50
Just five years after she left the University of Michigan to become a dancer in New York City, Madonna Louise Ciccone made her first move as a worldwide trendsetter – stacking her black rubber bracelets and flashing her crop top for TV’s Solid Gold while performing “Holiday” in 1983.
2 of 50
Madonna played it sweet and tough (check out that black leather!) as she starred as a street dancer turned fashion model in the video for 1984’s “Borderline.” Fun fact: Besides one very big bow, the clip also starred a then-unknown John Leguizamo as one of the singer’s pals.
3 of 50
After Madonna – clad in a tulle skirt, garters, a white bustier and a “Boy Toy” belt buckle – writhed her way through the 1984 MTV Video Music Awards, underwear was suddenly the new outerwear. “It’s not like I was saying, ‘Don’t pay attention to the clothes – to the lingerie – I’m wearing,’ ” she told Rolling Stone. “Actually, the fact that I was wearing those clothes was meant to drive home the point that you can be sexy and strong at the same time. In a way, it was necessary to wear the clothes.”
4 of 50
BIG SCREEN AMBITION
The movie was Desperately Seeking Susan, but after Madonna made her screen debut in the 1985 caper as a “free-spirited, adventurous femme fatale,” it was her gilded jacket that was in demand.
5 of 50
Paying homage to Marilyn Monroe’s performance of “Diamonds Are a Girl’s Best Friend” (from 1953’s Gentlemen Prefer Blondes), Madonna charmed suitors and picked up baubles in a slinky pink satin gown in the 1985 video for “Material Girl.” Although it wouldn’t be the last time she echoed Monroe, the pop star later said, “I don’t think I’m like Marilyn Monroe in a lot of ways. The main thing that we have in common is that we bleach our hair.”
6 of 50
Booties? Check. Lace leggings? Check. Miniskirt? Check. Madonna showed off her signature look during “Dress You Up,” the opening number for her first U.S. outing, 1985’s Virgin tour.
7 of 50
Only Madonna could shock with a make-under. The singer embraced her inner school marm in the 1986 video for “Live to Tell,” a song she wrote for then-husband Sean Penn’s film At Close Range. Although the movie flopped, the single topped Billboard’s Hot 100 chart.
8 of 50
In what would become a familiar sight, a dour-looking Sean Penn escorted Madonna – who mixed it up with an evening gown and a leather jacket – to the premiere of At Close Range. The couple’s nearly four-year marriage (they divorced in 1989) would become known for public spats and paparazzi standoffs. “I do believe we all have soulmates,” Madonna told PEOPLE. “I don’t believe that we necessarily end up with them.”
9 of 50
Winking at her Italian roots, Madonna boasted that “Italians Do It Better” in the controversial 1986 video for “Papa Don’t Preach,” which told the story of an unwed pregnant girl who decides to keep her baby. The video was also a star-making turn for Do the Right Thing actor Danny Aiello, who told PEOPLE the casting put him “on my way.”
10 of 50
Another day, another controversy! In the 1986 clip for “Open Your Heart,” Madonna played an exotic dancer – tassels, fishnets and all – who befriends a minor after he sneaks into her strip club. Although groups protested the use of the youth, Madonna later described the clip as a statement about innocence.
11 of 50
Madonna’s flirtation with the Spanish language and Latin culture began with the bilingual hit “La Isla Bonita.” In the 1987 video, the newly brunette singer dances in a red ruffled flamenco dress to the sounds of guitar.
12 of 50
In the 1987 crime romp Who’s That Girl, Madonna played a spunky but ditzy ex-con named Nikki wearing – what else? – a leather jacket, fingerless gloves and a miniskirt. “There was just something about the character – the contrasts in her nature, how she was tough on one side and vulnerable on the other – that I thought I could take and make my own,” she told Rolling Stone.
13 of 50
A steamy embrace with a saint, a burning cross and a loose shoulder strap would all add up to one of the pop singer’s biggest media storms. After the debut of “Like a Prayer” on March 3, 1989, the Vatican banned her from performing in Italy and Pepsi dropped her from its ad campaign – but Madonna kept her reported $5 million fee.
14 of 50
In matching painted denim cutoffs and jeweled bras, Madonna and then-pal comedienne Sandra Bernhardt performed a raunchy rendition of the Sonny and Cher classic “I Got You Babe” at an AIDS benefit in 1989.
15 of 50
As the ’80s drew to a close, Madonna – fresh from filing for divorce from Sean Penn – ditched her feminine style and debuted a bold, androgynous look. Standing tall in menswear and brandishing a monocle, the singer flexed her muscles (literally), flashed her bra and seduced a sweaty factory worker in the epic video for “Express Yourself.”
16 of 50
A softer side of the singer emerged from the surf in the video for “Cherish,” Madonna’s surprisingly sweet 1989 love song. Directed by famed photographer Herb Ritts, Madonna – in a clingy black shirtdress – frolicked in the water and flirted with mermen.
17 of 50
No one can “strike a pose” like Madonna. Taking the dance craze out of New York’s gay underground and on the road, the singer vogued her way around the world on her 1990 Blonde Ambition tour in her iconic Jean Paul Gaultier cone bra.
18 of 50
As documented in the 1991 behind-the-scenes film Truth or Dare, the Blonde Ambition tour sparked protests from the Vatican to Canada. Among the show’s controversial elements: Her performance of “Like a Virgin,” during which the singer simulated masturbation while wearing a gold cone-topped corset.
19 of 50
Jean Paul Gaultier designed the costumes for Blonde Ambition, including this polka-dot getup for one of the tour’s frothiest numbers, a booty-bumping version of Madonna’s early hit “Holiday.”
20 of 50
Channeling the look of Marie Antoinette’s court at Versailles, Madonna thrilled the crowd at the 1990 MTV Video Music Awards with a lush, naughty performance of “Vogue.” Although the video snagged best direction, it lost video of the year (to Sinead O’Connor’s “Nothing Compares 2 U”).
21 of 50
Madonna was sleek and sexy as ’50s-era nightclub siren Breathless Mahoney in the 1990 live-action comic-book flick Dick Tracy. Although the film wasn’t a hit, I’m Breathless, Madonna’s album of songs from and inspired by the movie, eventually went double-platinum, thanks to hits like “Vogue” and “Hanky Panky.”
22 of 50
After gossip spread that Madonna was hooking up with her Dick Tracy costar, legendary playboy Warren Beatty, the twosome stepped out, hand-in-hand, at the film’s Washington, D.C., premiere in 1990. But Madonna stole the spotlight – sporting flowers in her hair, chunky shoes and a babydoll dress, long before Courtney Love would pair the look with grunge.
23 of 50
She may have be dripping in $20 million Harry Winston diamonds, but it was neither her bling, nor her daringly low-cut Bob Mackie gown, that had people talking at the 1991 Academy Awards. Madonna arrived with Michael Jackson, and whispered and giggled in his ear at the post-show bash at Spago. But it was all just for show, with Madonna soon ditching the King of Pop for beau Warren Beatty.
24 of 50
In a Jean Paul Gaultier cone bra and miniskirt (similar to the black ones he had designed for her Blonde Ambition tour), a brunette Madonna made a grand entrance at the 1991 Cannes International Film Festival for the premiere of Truth or Dare.
25 of 50
There may be no crying in baseball, but there sure are short skirts! In the 1992 hit A League of Their Own, Madonna starred as “All the Way Mae,” a center-fielder for the Rockford Peaches in the WWII-era baseball movie. The film also starred Tom Hanks, Geena Davis and Rosie O’Donnell, who became a close pal of the pop star.
26 of 50
BREAST IN SHOW
Madonna got something off her chest – her top! – at Jean-Paul Gaultier’s fall runway show in 1992. The topless singer joined fellow stars like Billy Idol and Faye Dunaway at the charity event, which raised $750,000 – along with eyebrows – for amfAR (the American Foundation for AIDS Research).
27 of 50
Dressed as a vampy version of Little Bo Peep – down to the stuffed toy lamb in her arms – Madonna arrived at the Oct. 15, 1992, release party for her scandalous coffee-table book, Sex. The bash, held in New York’s then-seedy meatpacking district, featured models acting out fetish fantasies with whips and handcuffs, and some just reclining in tubs filled with caramel corn.
28 of 50
Touring in support of her sexually charged album Erotica, a leather-clad Madonna presented The Girlie Show, a naughty burlesque-themed tour that featured topless dancers, clowns and a simulated orgy during “Deeper and Deeper.” One of her featured dancers included Dancing with the Stars judge Carrie Ann Inaba, who performed topless.
29 of 50
NOTHING BUT NET
Going back to her love affair with Spanish culture, Madonna played the part of a woman obsessed with a bullfighter in the 1994 video for “Take a Bow.” The ballad, from her album Bedtime Stories, was Madonna’s longest-running No. 1 hit, topping the charts for seven weeks. The romantic and retro video – part of her campaign to win the film role of Evita – was a marked departure from the singer’s Erotica-era sexualized persona.
30 of 50
Madonna returned to sexual imagery with the 1995 video for “Human Nature,” a tongue-in-cheek look at bondage that acted as a response to critics of her Sex book. Squeezed into a latex bodysuit and wearing cornrows, Madonna alternately wields a whip, is bound to a chair and poses with a Chihuahua – in matching latex.
31 of 50
The singer went ’40s glam in elegant suits and hats as beloved Argentinean presidential wife Eva Péron in the 1996 musical film Evita. During filming, Madonna discovered she was pregnant with daughter Lourdes. “It got hard toward the end, just in terms of working long hours and being on my feet,” Madonna said. “But it was okay, I got through it.”
32 of 50
A WINNER AT LAST
The pop star flaunted her post-baby curves in a plunging Dolce & Gabbana bustier gown at the Jan. 19, 1997, Golden Globes, where she won best performance by an actress for Evita. After the show, Madonna mentioned her real lucky charm – daughter Lourdes, born on Oct. 14. “She brings me the most luck,” the singer said backstage.
33 of 50
SEEING THE 'LIGHT'
The new mom – and new devotee of Kabbalah – played it simple in a denim jacket, softly waved hair and now-omnipresent red-string bracelet in the video for “Ray of Light,” the lead single off the like-titled 1998 album. “It’s really great,” she told Kurt Loder about her newfound religion. “The whole idea of cause and effect, for every action there’s a reaction: It’s like, you pull in what you put out, basically. If you want to have goodness in your life, you have to give it.”
34 of 50
Madonna embraced the Far East for her show-opening version of “Nothing Really Matters” at the 1999 Grammy Awards in L.A., where she finally won. Accepting the Grammy for best pop album in her red Gaultier kimono, the toned-down singer thanked her coproducers and cowriters.
35 of 50
For the movie The Next Best Thing, which starred Madonna and Rupert Everett, the singer recorded a cover of Don McLean’s classic “American Pie.” The remake, released in February 2000, would became her first single of the new millennium. The video had a simple concept: an all-American Madonna dancing around with a U.S. flag in blue jeans and a tiara.
36 of 50
Two years after welcoming Lourdes, Madonna, who had tamed her wild side with motherhood, was pregnant again in May 2000. This time, she was expecting son Rocco, born Aug. 11, with movie director Guy Ritchie.
37 of 50
From earth mother to rhinestone cowgirl: “Music,” the first release off her new album by the same name, had the then-pregnant singer back in the clubs – at least in her video – in a white fur coat and a wide-brimmed hat. Fun fact: The gold limo that shuttled Madonna and her friends in the 2000 clip was driven by Sacha Baron Cohen, a.k.a. Ali G, then virtually unknown in the U.S.
38 of 50
Madonna – in Dsquared leather cowboy shirts – took her western inspiration and kicked it up in the video for her next single, “Don’t Tell Me,” which featured plenty of boot-scootin’ and line dancing.
39 of 50
At the January 2001 premiere of Guy Ritchie’s Snatch, Madonna splashed her new name across her back: Mrs. Ritchie. The singer married the director at the Great Hall of Scotland’s 19th-century Skibo Castle on Dec. 22 in a Stella McCartney-designed dress. A 4-year-old Lourdes was a flower girl, and Rocco sat with a nanny in the front row.
40 of 50
Before embarking on her 2001 Drowned World tour – her first since 1993 – Madonna performed a show at New York’s Roseland Ballroom in a T-shirt giving a nod to another chart-topping lady. “Britney Spears became my talisman for the week,” Madonna told Elle in 2001. “I became obsessed with wearing [Britney] T-shirts. I slept in them, as well. It was like I felt it would bring me luck. And it did.”
41 of 50
When the Drowned World tour kicked off in September 2001, the club girl proved herself a rock star, coming out in punk-inspired costumes and bearing her own six-string. “I kept saying to myself, ‘What am I f–ing doing? Who am I kidding? I just learned how to play guitar! Why am I doing this?’ ” Madonna said at the time.
42 of 50
THE KISS SEEN 'ROUND THE WORLD
Paying homage to Madonna’s classic VMA performance of “Like a Virgin,” Britney Spears and Christina Aguilera gave the hit a whirl before the icon herself made a grand entrance. In a military-inspired outfit – the theme of her American Life album – Madonna sang her new single “Hollywood” before locking lips with both popsters.
43 of 50
WILD 'ENGLISH ROSE'
Looking more “Live to Tell” than “Like a Virgin,” Madonna covered up in a conservative Prada floral frock for the Sept. 14, 2003, launch of her children’s book, The English Roses. The new author sat on a swing at London’s Kensington Roof Gardens between children Lourdes, then 6, and Rocco, then 3, and read passages from the book, about school friends who are jealous of another girl.
44 of 50
Winking at the “Italians Do It Better” shirt she wore in the “Papa Don’t Preach” video, Madonna proudly proclaimed that “Kabbalists Do It Better” during the finale of her 2004 Reinvention tour.
45 of 50
NUN OF THAT
Madonna outraged Catholic leaders yet again when she and husband Guy Ritchie dressed up as a nun and the Pope for a London costume party celebrating the Jewish holiday of Purim in March 2004. Madonna’s rep Liz Rosenberg said, “They meant no disrespect at all.”
46 of 50
Sporting a purple leotard similar to her cover outfit on her 10th studio disc, Confessions on a Dance Floor, Madonna promoted the ’70s-inspired dance album at G-A-Y, a weekly party at London club Astoria, in November 2005.
47 of 50
GETTING HER POINT ACROSS
The singer’s decision to perform “Live to Tell” while mock-crucified was – not surprisingly – the most controversial element of her 2006 Confessions tour. After the Vatican condemned her as blasphemous, the singer issued a statement, saying, “My performance is neither anti-Christian, sacrilegious or blasphemous. Rather, it is my plea to the audience to encourage mankind to help one another and to see the world as a unified whole.” She added, “I believe in my heart that if Jesus were alive today he would be doing the same thing.”
48 of 50
ON THE RIGHT TRACK
The yoga aficionado and dedicated gym rat modeled samples from her eponymous clothing line for H&M in the streets of London. The singer – wearing the white track suit she sported in advertisements for the line – offered trench coats, other track suits, sleek dresses and more for affordable prices.
49 of 50
A MOVING MOMENT
Chic in Chanel haute couture, Madonna premiered her documentary I Am Because We Are, about orphans in Malawi, at the Cannes Film Festival this past May. The work was inspired by her own experience of adopting a Malawian boy, David Banda. “This is a film I want the world to see,” a choked-up Madonna told the audience.
50 of 50
A TRUE FIGHTER
A tough-to-beat champ on – and off – the stage, Madonna suited up as a heavyweight boxer in press photos for Hard Candy, her 11th studio album, which was released 25 years after that first Solid Gold appearance. Now 50, Madonna’s embarking on yet another ambitious tour. “I’m not sure I can sing ‘Holiday’ or ‘Like a Virgin’ ever again,” the singer told New York’s Z100-FM. “I just can’t – unless somebody paid me like $30 million or something.”
Kelly Osbourne Spends 20 Minutes Trying to Get Out of an Ill-fitting Sample Size Dress
Paris Jackson Shows Off Tattoo in Memory of Late Father Michael Jackson
We Tried It: Juvederm Volbella XC, a New Lip Injection That Lasts a Whole Year
Jennifer Lawrence Just Wore the Coolest $25,000 Scarf Necklace - and You Can Get the Look for a Fraction of the Price