Rags to Riches: The Madonna Story You Never Knew
By Jack Ripley | October 18, 2023
Madonna Moved to New York To Become A Dancer, 1978
Welcome to a visual journey of the Material Girl! From her religious start in Michigan, to the gritty streets of New York City, to the dazzling heights of pop royalty, this electrifying photo gallery charts the meteoric rise and lasting legacy of the one and only Madonna. Prepare to be mesmerized as you witness the evolution of an icon who defied convention, broke boundaries, and redefined the world of music and fashion. Get ready to strike a pose and join us in celebrating the Queen of Pop's extraordinary journey.
At age 20, after dropping out of college, Madonna left Michigan and moved to New York City all on her own. She had been attending University Of Michigan on a dance scholarship, and intended to continue to pursue her career in modern dance, on her own terms. Although the move was scary, she soon found work as a background dancer.
It was the first time I'd ever taken a plane, the first time I'd ever gotten a taxi cab. I came here with $35 in my pocket. It was the bravest thing I'd ever done.
Madonna Was an Art Model to pay the bills, 1978
After moving to New York City on her own, money was tight for Madonna. She began posing for photography classes at Parsons School of Design as an additional source of income, along with working at Dunkin' Donuts. She was paid as little as $25 for each photography session. Unfortunately, in 1985 some racier magazines dug up and published these photos in order to create scandal. In response, Madonna bravely and simply said:
"I'm not ashamed."
Madonna Is Her Real Name!
Born Madonna Louise Ciccone in 1978, Madonna was the third of six children to Madonna Louise and Silvio Anthony "Tony" Ciccone. She was nicknamed "Little Nonnie" by family members. As a middle child, Madonna often found herself feeling overlooked and craving attention:
You want your parents' attention ... You don't want the hand-me-down clothes ... You want to stand out. You want to be treated special.
Madonna Was A Straight-A Student, 1970's
Throughout her school years, Madonna always got great grades! She attended St. Frederick's and St. Andrew's Catholic Elementary Schools, then West Middle School, and Rochester Adams High School, with straight A's all the way through. She said:
I wasn't rebellious in a certain way. I cared about being good at something. I didn't shave my underarms and I didn't wear make-up like normal girls do. But I studied and I got good grades... I wanted to be somebody.
Her Mother Died When Madonna was Five, and She Never Forgave Her Father, 1963
Madonna's mother, Madonna Louise, passed away from cancer in 1963. Three years later, her father, Tony, got remarried - to the family's housekeeper, Joan Gustafson. The couple had two children, Mario and Jennifer. Madonna felt that this marriage was a betrayal to her mother, and it seriously strained her relationship with Tony.
Her Interest in Dance Started in Ballet
Although Madonna's dad originally had her in piano lessons, she convinced him to switch her over to ballet, where her love of dance blossomed. Her teacher, Christopher Flynn, encouraged her to follow her passion for dance. After her years at University of Michigan on a dance scholarship, she then took classes at the Alvin Ailey American Dance Theater in New York. She eventually danced with the famed Pearl Lang Dance Theater in New York City before pursuing a career in music.
She Had An Ugly Break-Up With Jean-Michel Basquiat, 1982
In the early 1980s, before Madonna became the Material Girl we all know and love, she was an aspiring dancer and singer making her way in New York City. During this time, she crossed paths with Jean-Michel Basquiat, a charismatic and influential artist who was at the forefront of the Neo-Expressionism movement. In a city teeming with artistic expression, the pair reportedly dated for a brief period. During this time, Basquiat's art was beginning to receive significant attention, while Madonna was still working her way up the ladder in the music industry. Sadly, though, this power couple relationship was not meant to last. According to the Material Girl herself, they broke up due to Basquiat's substance abuse issues, and he destroyed the paintings he had made for her:
He wouldn’t stop doing heroin. He was an amazing man and deeply talented, I loved him. When I broke up with him he made me give [the paintings he gave me] back to him. And then he painted over them black.
Her Debut Single Was "Everybody", 1983
Madonna made her grand entrance into the music industry with her energetic debut single, "Everybody". She initially pitched a different song called "Ain't No Big Deal" to Sire Records. However, the label executives were more drawn to the captivating energy of "Everybody" and decided to release it as her first single. And as they say, the rest is history!
Her First Breakthrough Hit Was "Holiday", But She Didn't Write It, 1983
"Holiday" was initially written by Curtis Hudson and Lisa Stevens of the group Pure Energy, who had hoped to secure the song for another artist. However, fate had other plans, as Sire Records' executive Michael Ostin discovered the catchy tune and recognized its potential as the perfect song for the label's rising star, Madonna. It didn't take long for the Material Girl to put her unique spin on the track, creating an instant dance-pop classic. "Holiday" went on to peak at No. 16 on the Billboard Hot 100 chart, cementing Madonna's status as a force to be reckoned with in the music industry.
Like A Virgin was #1 on the Billboard Hot 100 For Six Weeks Straight, 1984
In 1984, a young and ambitious Madonna set the world ablaze with her second studio album, Like a Virgin, with the album's title track quickly became a pop culture phenomenon. The tune's bouncy melody and Madonna's playful vocals turned "Like a Virgin" into an instant earworm, making it a defining moment in the Queen of Pop's illustrious career. As the song climbed the charts, it became clear that the world was ready to embrace Madonna's provocative and flirtatious persona.
She Made A Scene At The MTV VMA's, 1984
In 1984, Madonna delivered a now-iconic performance at the MTV Video Music Awards that would not only define her career but also stir controversy. During her performance, Madonna appeared in a wedding dress, complete with a "Boy Toy" belt, setting the stage for a bold and daring act. The show took a scandalous turn when Madonna began to roll around on the floor, suggestively writhing and exposing her underwear. This display of overt sexuality, especially in the context of a wedding dress, shocked audiences and made headlines. The kicker? She was actually on the floor trying to recover her stiletto shoes, which had come off when she emerged from the wedding cake earlier in the performance:
So I thought, ‘Well, I'll just pretend I meant to do this,’ and I dove on the floor and I rolled around...I didn't even know that my butt was showing.
She Starred In "Desperately Seeking Susan", 1985
In Desperately Seeking Susan, directed by Susan Seidelman, Madonna stars as Susan Thomas, a free-spirited, enigmatic woman whose life becomes intertwined with that of the bored suburban housewife, Roberta Glass, played by Rosanna Arquette. After a case of mistaken identity, Roberta becomes embroiled in a series of comedic and dangerous situations as she tries to unravel the mystery surrounding Susan. Madonna's performance in the film was praised for her ability to bring authenticity and charm to the character of Susan. The film's success also helped to boost Madonna's music career, as the movie featured her hit single "Into the Groove."
Madonna Performed At Live Aid, 1985
At Live Aid 1985, the Queen Of Pop performed a set of three songs - “Holiday,” “Into the Groove” and “Love Makes the World Go Round”. She was introduced cheekily by Bette Midler:
I want you to know I have no idea why I was asked to introduce this next act — because you all know, I am the soul of good taste and decorum. However we are thrilled to be able to introduce to you today a woman whose name has been on everyone’s lips for the last six months. A woman who pulled herself up by her bra straps and has been known to let them down occasionally.
"Crazy For You" Was Written For A Movie, 1985
Madonna originally recorded her hit song "Crazy For You" for the 1985 coming-of-age movie Vision Quest, starring Matthew Modine. The material girl even makes a cameo as a club singer in the movie! And guess what's she's singing? Of course, the "ultimate slow-dance song" - "Crazy For You".
Planned Parenthood Hated "Papa Don't Preach", 1986
Who hasn't Madonna ticked off, at this point? In 1986, though, it wasn't religious leaders or the Vatican. Planned Parenthood felt that Madonna's new song, "Papa Don't Preach", was spreading an irresponsible method about pregnancy. Planned Parenthood explained their reasoning as such:
The message [of "Papa Don't Preach"] 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 — don't preach to me, Papa.
Madonna Was Married To Sean Penn In The Late '80s
In 1985, Madonna and Sean Penn first crossed paths on the set for the "Material Girl" music video, and married just a few months later on Madonna's 27th birthday. In 1986, Madonna released her critically acclaimed album True Blue, which was dedicated to Sean Penn, further solidifying their status as a power couple. However, despite their love for one another, the couple couldn't escape the challenges that their marriage faced. Both Madonna and Sean Penn had strong personalities, which led to frequent clashes and disagreements, and they finally called it quits in 1989. Though some reports say that Penn had been physically abusive to Madonna during the marriage, the two appear to be on good terms now.
Madonna Used Her Voice During The Aids Crisis, 1980s
n the 1980s and '90s, as the AIDS crisis ravaged communities and stigmatized those affected by the disease, many public figures shied away from addressing the issue. But for Madonna, turning a blind eye was never an option. She had lost many friends and colleagues to the disease, including her close friend and mentor Martin Burgoyne, and her frequent artistic collaborator Keith Haring. She got involved with organizations such as amfAR (The Foundation for AIDS Research) and consistently donated proceeds from her concerts, album sales, and merchandise to support HIV/AIDS research and advocacy. Even her Like A Prayer album included an AIDS fact card. She said:
During the AIDS epidemic, I was getting involved with a lot of groups and speaking up and I was enraged by how I saw people being treated. I came to the LGBTQ community and put my arms around them. While everyone else was running away from them, I was running towards them.
Madonna's "Like A Prayer" Video Was Pretty Controversial, 1989
In 1989, Madonna shook the world once again with her single "Like a Prayer." The Queen of Pop didn't just release another catchy tune; she also dropped a music video that had the world clutching its pearls and reaching for the smelling salts. The video combined religious imagery with a narrative about racial injustice and redemption. The video starred Madonna as a witness to a crime, a steamy kiss with a saint, and a dancer in a church. The provocative imagery in the "Like a Prayer" music video sparked a massive controversy, with religious groups accusing Madonna of blasphemy and mocking their faith. The public outcry reached such a fever pitch that even major corporations felt the heat. Pepsi, which had recently signed a $5 million endorsement deal with Madonna, pulled their TV commercial featuring the song and swiftly canceled their contract with the pop star.
"Justify My Love" Was Banned From MTV, 1990
In 1990, the Queen of Pop was once again at the epicenter of a media storm, this time for the release of her music video for "Justify My Love". The video, directed by Jean-Baptiste Mondino, featured Madonna and many others in various states of undress, exploring their desires in the dimly lit corridors of a Parisian hotel. The erotic imagery, including scenes of voyeurism, and androgyny, pushed the boundaries of what was deemed acceptable for mainstream music videos at the time. The provocative nature of the "Justify My Love" music video led MTV to ban the video from their network, deeming it too explicit for their audience. Though some insisted it was just a publicity stunt, Madonna was steadfast that the controversy was unplanned:
It may seem like it was a publicity stunt, and I was very lucky, I must say. But I did not plan on selling this video The controversy just happened. It wasn’t planned. So lucky me.
She Created A Gay Anthem With "Vogue", 1990
Strike a pose! When Madonna released "Vogue" in 1990, it was already a phenomenon. But when she performed it live at the MTV Awards later that year? It was a theatrical spectacle that brought the spirit of 18th-century French aristocracy to a 20th-century pop music stage. Madonna, as Marie Antoinette surrounded by courtiers, delivered a flawless performance that celebrated the vibrant dance culture of vogueing. The choreography was tight, the energy was high, and Madonna, in true Madonna style, commanded the stage with her magnetic presence. Honestly, you'll have to watch it to get it.
She Brought Back The Cone Bra, 1990
The cone bra, with its structured design accentuating the bust, was seen as the epitome of glamour and sex appeal in the post-war era of the 1940s and 1950s, but quickly fell out of fashion - that is, until Madonna. Madonna's version, crafted by the avant-garde genius Jean Paul Gaultier, took the original design and gave it a futuristic, exaggerated twist. The bullet bra became synonymous with Madonna's provocative style and the 1990 Blond Ambition Tour, featuring prominently in her "Express Yourself" performance. It challenged societal norms around female sexuality and quickly became a symbol of empowerment. Today, the bullet bra remains one of the most iconic pieces of fashion in pop music history.
She Channeled Marilyn At The Oscars, 1991
The Material Girl took the Oscars Stage in 1991, wowing celebrities and audiences at home alike. Her performance of "Sooner or Later" was more than just a song; it was a complete tribute to the sultry allure of Hollywood's golden age. The song, written by Stephen Sondheim, won the Oscar for Best Original Song that year, and Madonna's performance remains one of the most memorable moments in Oscar history.
Channeling Marilyn Monroe was a bold move. But, of course, if there's one thing Madonna is known for, it's bold moves, and she pulled it off. Dressed in a sparkling, white, sequined gown with a voluptuous fur boa, her blonde hair styled in Monroe's signature waves, and her red lips juxtaposed against her long, seductive, white gloves, Madonna didn't just channel Monroe, she fully embodied her.
She Dated Michael Jackson, 1991
Though Madonna met Michael Jackson way back in the 1980s, sparks didn't begin to fly until a decade later:
I met him in the 80s, when I first started working with my manager, Freddy DeMann, who at the time was managing Michael Jackson. I saw him play at Madison Square Garden and I was blown away. He was flawless. There was a party at the Helmsley Palace Hotel. He was very shy, but it was a thrill for me.
The two attempted a relationship, going on dates, one of which was even at the 1991 Oscars. Madonna later admitted the two (at least) kissed that night. However, creative differences while attempting to collaborate on a song, "In The Closet", eventually drove them apart. Their brief moment as a potential pop power couple? Just another fascinating footnote in the annals of pop music history.
She Released A Coffee Table Book Called "Sex", 1992
In 1992, the Queen of Pop decided to take her provocative persona to new heights with the release of her book, Sex. Sex was no ordinary book; it was a luxurious visual feast, packed with steamy, black-and-white photographs shot by famed fashion photographer Steven Meisel. The photos featured Madonna alongside an array of models, actors, and celebrities, such as Naomi Campbell, Vanilla Ice, and Isabella Rossellini, engaging in a variety of risqué and erotic scenarios. Unsurprisingly, Sex sparked a media frenzy and was met with polarizing opinions. Critics called it obscene, vulgar, and a desperate bid for attention, while others praised its unapologetic exploration of sexuality and boundary-pushing nature. Sure seems like an interesting read either way!
A Lot of Celebrities Appeared in The Music Video For "Erotica", 1992
The "Erotica" music video made a lot of waves - what Madonna production didn't? Directed by Fabien Baron, and featuring extremely racy content, "Erotica" only aired on MTV three times before being completely banned. It contained a lot of behind the scenes shots from the making of Madonna's coffee table book, Sex, and was pretty studded. Model Naomi Campbell and actress Isabella Rossellini made appearances, among others!
Sex Ended Her Relationship With Vanilla Ice, 1992
The book Sex, that is. Madonna had been dating Robert Van Winkle, better known by his rapper name "Vanilla Ice", when she released her eyebrow-raising book Sex. Ice was not pleased by the scandalous nature of the book:
"I broke up with her after she printed that book because I was hurt to be an unwitting part of this ****** package. It was disgusting and cheap. We were in a, relationship yet it looked like she was screwing all these other people. I thought she was taking pictures and running 'round naked because she was like that. Then when the book came out I was so embarrassed and ashamed...She threw me in like I was a product off a shelf and I didn't appreciate it. That was it and I ended it. She said she didn't have sex with these men but it looked like she was."
Madonna Also Dated Tupac Shakur in the 90's
In 2015, Madonna revealed that she had briefly dated musician and activist Tupac Shakur in 1993, only 3 years before his death. At the time, Madonna was thirty while Shakur was only 24. While the relationship did not last long, Shakur later wrote her a letter expressing regrets about how it ended, and explaining how he had felt he had been jeopardizing his career by dating an older white woman due to systemic racism.
I must apologize to you. Because like you said I haven’t been the kind of friend I know I am capable of being. Not because I am evil or because you weren’t worthy but at the risk of sounding over dramatic, the effects of racism make it difficult for a young black man to properly show affection for an older white woman...For you to be seen with a black man wouldn’t in any way jeopardize your career. But for me, at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was.
She Gave David Letterman Her Underwear, 1994
Few moments have been as memorable in talk show history as Madonna's appearance on "The Late Show with David Letterman" on March 31, 1994. Madonna dropped an F-bomb within the first few minutes, setting the tone for the rest of the segment. She used profanity a total of 14 times, despite Letterman's repeated attempts to steer the conversation in a more family-friendly direction. At one point, Madonna pulled out a pair of her underwear and dared Letterman to sniff it, though he refused. Afterwards, Madonna explained her behavior as a stand against TV censorship:
You can show a person getting blown up, and you can't say ****? It's such hypocrisy. The fact that everyone counted how many ***** I said—how small minded is that? ... The other thing that was ridiculous was that David Letterman knew I was going to do it. I talked to the producers of the show. Everybody was like, this will be really funny if you say **** a lot they'll just keep bleeping you. Well, I came out and started doing it, and David freaked out. The way he introduced me was derogatory, so my whole thing was, okay, if that's how you want to play it, you cannot beat me at this game.
She Dated Dennis Rodman in the Early '90s
Madonna and athlete Dennis Rodman had a short-lived but apparently intense fling circa 1994. Rodman had some interesting things to say about their relationship in his autobiography, Bad As I Wanna Be, including his take on their sex life:
Madonna talked all the time about having a baby. I think she wanted every bit of Dennis Rodman--marriage, kids, everything...[intimacy with Madonna] was just very entertaining. She wasn't an acrobat, but she wasn't a dead fish either.
Madonna Starred In The Musical Film Evita, 1996
In 1996, the musical film Evita brought the captivating story of Argentine First Lady Eva Perón to the silver screen, and it was none other than the Queen of Pop, Madonna, who took on the challenging role of the iconic figure. She underwent rigorous vocal training with a top-notch vocal coach to perfect her singing for the demanding role. Her hard work paid off, as the film's soundtrack won the Academy Award for Best Original Song for "You Must Love Me".
In 1999, She Founded The Ray Of Light Foundation
Established by Madonna in 1998, the Ray Of Light Foundation aims to improve the lives of vulnerable communities worldwide. Named after her introspective and spiritually-infused 1998 album, the Ray of Light Foundation was born out of Madonna's desire to give back and make a tangible impact on the lives of those in need. The foundation focuses on supporting initiatives in the areas of education, health, and women's rights, with a special emphasis on helping children and disadvantaged communities around the world. The Ray of Light Foundation has funded and supported projects in various countries, including Malawi, Afghanistan, Pakistan, Haiti, and the United States. Madonna's commitment to improving the lives of vulnerable children has been particularly evident in her work in Malawi, where the foundation has helped to build schools and provide access to quality education for thousands of students.
She Married Director Guy Ritchie, 2000
It was through mutual friends, singer Sting and his wife Trudie Styler, that Madonna and Guy first met at a dinner party. Their relationship progressed rapidly, and by the end of 2000, they welcomed their son Rocco into the world.
They tied the knot just a few months later in a lavish ceremony at Skibo Castle in Scotland, with a plethora of celebrity guests in attendance. During their marriage, Guy directed the music video for Madonna's single "What It Feels Like for a Girl", while Madonna starred in Guy's film Swept Away, which unfortunately was a flop. p. In October 2008, after nearly eight years of marriage, Madonna and Guy Ritchie announced their separation, but maintained a relatively civilized split. The couple agreed to share custody of their children, and Guy was reportedly granted a settlement of between £50 and £60 million.
She Locked Lips With Britney Spears at the VMAs, 2003
The world was shocked and titillated in 2003 when, at the MTV Video Music Awards, The Queen of Pop and the Princess of Pop shared a steamy kiss in front of everyone. Madonna and Britney Spears, along with Christina Aguilera, were performing two Madonna hits - "Like A Virgin" and "Hollywood" on a wedding-themed set, when the two locked lips. Is it getting hot in here?
Christina Aguilera Got A Kiss, Too!
After planting one on Britney at the 2003 VMAs, Madonna turned around (literally) and smooched singer Christina Aguilera, too. While many viewers were shocked and scandalized, Christina Aguilera couldn't care less:
Shock value gets more and more extreme or whatever. But honestly, at the time, yeah, I never thought anything of it. It was like, 'Okay, it's two girls kissing.' It wasn't shocking back then. It's not shocking now, to me.
Her "Confessions" Tour Angered Religious Leaders, 2006
One of the most talked-about moments of the Confessions Tour was Madonna's performance of her hit "Live to Tell." The Queen of Pop, clad in a crown of thorns, sang the emotional ballad while suspended from a giant mirrored cross. The provocative scene sparked outrage among religious groups, who accused Madonna of blasphemy and disrespecting their faith. Madonna maintained that her performance was not meant to be offensive:
My 'confession' follows and takes place on a Crucifix that I ultimately come down from. This is not a mocking of the church.
Madonna Has A Strong Artistic Relationship With Religious Imagery
Madonna was raised in a Catholic family that was very religious. Her parents had many friends who were nuns and priests, and she was even confirmed - she chose Veronica as her confirmation name. It's no surprise, then, that Catholicism, and her rebellion against it has had a huge affect on her art. Unfortunately, this has caused some blowback, as catholic leaders and the Vatican have found the use of Catholic symbols in her work offensive. Madonna's costume designer, Marlene Stewart, has spoken on how she thinks Madonna still uses the symbolism in a reverent way:
From the beginning, she really had her cultural heritage steeped in Italian Catholicism and the Catholic Church. It has been a big part of her artistic expression. I think [Like A Prayer] shows a certain reverence and it consumes her life and being, but at the same time, she co-mingles it with ideas of sexual ecstasy and religious ecstasy.
She Published A Children's Book, Mr. Peabody's Apples, 2003
When you think of Madonna, children's literature might not be the first thing that comes to mind. However, in 2003, the Material Girl surprised everyone by releasing her children's book, Mr. Peabody's Apples. he book tells the story of Mr. Peabody, a beloved teacher and Little League coach, who is falsely accused of stealing an apple by a young boy named Tommy Tittlebottom. As the rumor spreads through the town, Mr. Peabody's reputation is tarnished. To teach Tommy the impact of spreading rumors, Mr. Peabody asks him to bring a pillow full of feathers to the baseball field and release the feathers into the wind. The lesson? Just like the scattered feathers, once a rumor is spread, it's nearly impossible to undo the damage.
Madonna Headlined the Most-Watched Super Bowl Halftime Show, 2012
With a breathtaking, ancient Egyptian-themed stage design and a jaw-dropping entrance befitting a queen, Madonna took the field at Lucas Oil Stadium, accompanied by a legion of dancers and performers. The 12-minute show was a star-studded affair, featuring guest appearances by musical powerhouses like LMFAO, Nicki Minaj, M.I.A., and CeeLo Green, who joined Madonna in a breathtaking rendition of "Like a Prayer" that brought the house down. The performance set a new record, becoming the most-watched Super Bowl halftime show in history, with a staggering 114 million viewers tuning in. This record was later surpassed by Katy Perry in 2015, but Madonna's groundbreaking performance remains a benchmark for Super Bowl entertainment.
She Was Crowned Billboard's Woman Of The Year, 2016
In a testament to her incredible career and enduring influence, Madonna was honored with the prestigious title of Woman of the Year at the 2016 Billboard Women in Music event. This accolade acknowledged not only her musical achievements but also her lasting impact on the entertainment industry, philanthropic endeavors, and her unyielding advocacy for social change. As of 2016, Madonna had released 13 studio albums, earned 46 No. 1 hits on the Dance Club Songs chart, and sold over 300 million records worldwide. Throughout her career, she has been a staunch advocate for women's rights, LGBTQ+ rights, and social justice, often using her platform to address important issues and promote change.
Madonna's Always Gonna Make Waves
As of 2023, Madonna's still going strong, with outfits and choices that keep people on their toes. Whether the reason is her risqué music, steamy coffee-table books, or dating people 40 years her junior, Madonna is convinced she is always going to be a topic of conversation:
I don’t get it. Everything I do is controversial. Nothing’s changed – I’m still in trouble.