Madonna's life and career in pictures

Shock and awe: That pretty much sums up how we feel about Madonna. No one has yet been able to combine talent and ambition with controversy and reinvention in quite the same way she has — all while managing to keep the world watching well into her fourth decade as a professional performer. The Material Girl showcases yet another side of herself in her new documentary, "Madame X," which debuted on Paramount+ and on MTV on Oct. 8, 2021. To mark the occasion, Wonderwall.com is taking a walk down memory lane and celebrating a life that's often imitated, but never duplicated.

Keep reading to take a look back at Madonna's life and career in pictures…

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Madonna Louise Veronica Ciccone was born on Aug. 16, 1958, in a suburb of Detroit, the eldest daughter among five siblings in Madonna and Silvio Ciccone's tight-knit Italian-Catholic family. Her mother died after a battle with breast cancer when Madonna was just 5, an event that continues to shape her life. "The anguish of losing my mother left me with a certain kind of loneliness and an incredible longing for something. If I hadn't had that emptiness, I wouldn't have been so driven," Madonna told Scotland's No. 1 magazine in 2012. "Her death had a lot to do with me saying, after I got over my heartache, I'm going to be really strong if I can't have my mother. I'm going to take care of myself."

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Madonna was a cheerleader in high school (seen here in 1974) as well as an honor student. "I studied and I got good grades," she told Vanity Fair. "I wanted to be somebody." Two years after enrolling at the University of Michigan on a dance scholarship, she dropped out and moved to New York City to pursue her dream of being a professional dancer.

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Madonna (pictured in 1982) worked as a dancer, model and singer to make ends meet during her early days in New York City in the late '70s and early '80s. She formed two bands — Breakfast Club and Emmy — before getting her break as a solo artist when her song "Everybody" became a success on the club scene. "I thought everything was about having everyone adore you," she once told People. "I came to New York dreaming of becoming a professional dancer and somehow I fell into music. Everything following that was like, 'Oh my God! What's happening to my life?' You get caught up in that."

Madonna's career as a pop star exploded with the mainstream success for "Lucky Star" and "Holiday," but Madonna's performance of her controversial song "Like a Virgin" at the 1984 MTV Video Music Awards — the image of her writhing around on stage in a wedding dress and her now-infamous "boy toy" belt is seared into the brains of a generation — unleashed her first international pop-culture moment on the world.

After establishing herself as a music star, Madonna ventured into acting, playing a character who shared the same real-life sartorial instincts in 1985's "Desperately Seeking Susan" alongside Rosanna Arquette. The film not only spawned a hugely successful new song with Madonna's "Into the Groove" but also popularized the now-iconic lace-shirt-over-a-black-bra look paired with jelly bracelets — and lots of them.

Just as droves of women were stepping out in leggings, lace gloves and bows topping teased hair, Madonna began a never-ending physical metamorphosis: She chopped off her long hair in favor of a strikingly short, blonde crop cut that took center stage in her 1986 video for "Papa Don't Preach."

After meeting on the set of her "Material Girl" video, publicity-hungry Madonna and intensely private bad-boy actor Sean Penn embarked on a passionate romance and married in 1985 atop a cliff in Malibu. But the marriage, marked by violence and jealousy, was over just two years later. Asked about her then-husband by NBC's Jane Pauley in a 1987 interview, Madonna summed up their roller-coaster romance in two words: "Opposites attract." (The duo are pictured at a 1986 screening of his film "At Close Range.")

Madonna and Sean Penn's marriage wasn't their only failure. The couple also co-starred in 1986's "Shanghai Surprise," a film that was not only unsuccessful at the box office but also made the pop star a laughingstock in Hollywood. "I look back and think, 'Well, I invited it. I made some really stupid choices,'" she later told People. "It taught me to be more scrupulous."

The year 1987 was a huge one for Madonna: She made another movie, "Who's That Girl" (pictured), which fared far better than the disaster that had been "Shanghai Surprise." She embarked on a wildly successful world tour of the same name. And as the year drew to a close, she served Sean Penn with divorce papers.

Man-eater Madonna met her match when she started dating legendary Hollywood lothario Warren Beatty — who was two decades her senior — in 1990 after they co-starred in "Dick Tracy." He appeared in her groundbreaking 1991 documentary "Truth or Dare," in which he made his feelings about her attention-mongering lifestyle crystal clear. "There's nothing to say off camera," he said, mocking her. "Why would you say something if it's off camera? What point is there existing?" Fifteen months after their romance began, it was over.

Some of Madonna's greatest relationships were never romantic: Designer Jean Paul Gaultier created one of her most iconic looks: the pink cone-shaped brassiere that she wore during her Blonde Ambition tour in 1990. The famous garment sold for $52,000 at Christie's Pop Culture auction in 2012, cementing its status as one of pop music's most legendary looks.

Madonna cozied up to Vanilla Ice at a party following the premiere of her documentary "Truth or Dare" in Los Angeles on May 6, 1991. The duo were an item for about eight months before calling it quits in 1992 after she released her coffee table book "Sex," which displeased the rapper. "I broke up with her after she printed [the book] because I was hurt to be an unwitting part of this slutty package," he told News of the World. Ouch.

Madonna went brunette — and back in time — to play a female baseball player in 1992's "A League of Their Own." But in a letter she wrote to photographer pal Steven Meisel during filming in the Windy City, she didn't seem very excited about making the ensemble movie, which co-starred Geena Davis and Rosie O'Donnell. "I cannot suffer anymore than I have in the past month learning how to play baseball with a bunch of girls (yuk) in Chicago (double yuk)," she wrote. "I have a tan, I am dirty all day and I hardly ever wear make-up… And when God decided where the beautiful men were going to live in the world, he did not choose Chicago."

Madonna met personal trainer Carlos Leon in 1994 and two years later, they welcomed daughter Lourdes. While pregnant with Lola, Madonna filmed "Evita" and just two months after giving birth, attended its premiere looking slim again, with Carlos by her side. But the relationship wouldn't last: The pair split a few months after Madonna won a Golden Globe for her performance in "Evita." Perhaps surprisingly, there were no lingering hard feelings about the relationship's demise. "I have no regrets. I wouldn't change anything," Carlos told People in 2011. "I got the best thing out of that relationship, and that's my daughter. My daughter is everything to me."

Madonna beamed while posing with her award for best performance by an actress in a comedy or musical film for her performance as Eva Perón in the big-screen adaptation of the Andrew Lloyd Webber musical "Evita" during the 54th Annual Golden Globe Awards on Jan. 19, 1997.

Motherhood did little to slow Madonna, although it did make her more spiritual. She started following Kabbalah, a branch of Jewish mysticism, in the mid-'90s, and her newfound spirituality was a clear influence on her seventh studio album, "Ray of Light." Her chameleon-like transformation unfolded as she performed songs from the critically praised album, including "Nothing Really Matters" at the 1999 Grammy Awards costumed as a futuristic geisha.

Madonna cleaned up during the 41st Annual Grammy Awards in Los Angeles on Feb. 24, 1999. She took home three trophies for her "Ray of Light" album: best pop album, plus best dance recording and best short form music video for the title track. The album also won the Grammy for best recording package, though that trophy went to Madge's art director.

In 1999 — despite her affinity for patterned cowboy hats, like the one she wore to a Versace fashion show that September with Lola in tow — single mom Madonna found a new man. She was introduced to British director Guy Ritchie by Sting and Trudie Styler, and love bloomed. The following year, they made Lola a big sister with the birth of their first child together, son Rocco Ritchie.

Madonna and Guy Ritchie baptized son Rocco in Scotland days before their Christmastime wedding there in 2000, signaling the birth of a new era in the diva's life: lady of the manor. She earned a very British new nickname — Madge — and spoke in an odd yet distinctly English accent for years to come.

Guy Ritchie directed then-wife Madonna in his 2002 rom-com "Swept Away." It tanked at the box office and with critics alike, banking just $1 million on a $10 million budget and scoring a humiliating 5% fresh rating on Rotten Tomatoes — making it the auteur's most poorly reviewed offering yet … by far. The icy reception to the film prompted Madonna to put her acting career behind her. Since then, she's only acted three times: She had a small cameo in 2002's "Die Another Day," she popped up on a 2003 episode of "Will & Grace" and she voiced a character in 2006's "Arthur and the Invisibles."

Motherhood and marriage did little to quell Madonna's appetite for shocking her fans. At the 2003 MTV Video Music Awards, Madge shared an intimate kiss with a pop star desperate to follow in her footsteps — Britney Spears. But Madonna was far from ready to officially pass the torch to a new generation of pop stars; it was more like she was simply showing them how it's done.

Madonna shifted her musical focus again to establish herself as an electronic artist with the release of "Confessions on a Dance Floor" in 2005. She broke new ground again — and memorably made jaws drop as she flaunted her flawlessly toned body in a lavender leotard — when she performed its first single, "Hung Up," to open the 2006 Grammy Awards alongside a hologram of critically lauded band the Gorillaz.

Compelled by the plight of orphaned children in Malawi, Madonna started funding education programs there and, along with Guy Ritchie, adopted a child from the country — son David Banda — in 2006. Her new route to motherhood was not without controversy, however, as critics accused her of using her money and fame to circumvent laws requiring prospective parents to establish long-term residency in the poverty-stricken nation, which she visited with her little boy and daughter Lourdes Leon on April 17, 2007.

Madonna appeared by Guy Ritchie's side at the September 2008 premiere of his film "RocknRolla," but a month later, they confirmed their marriage was over. "When you start off, everything's great and lovely, and the person you've married is flawless, and you're flawless," Madonna told Newsweek in 2012, giving rare insight into her relationship with the director, who's 11 years her junior. "Then time goes by, and you share a life, you have children, and there are cracks in the veneer. It's not as romantic as it used to be. You think, 'This isn't what I thought it was going to be,' and 'How much am I willing to sacrifice?'"

In 2009 — three years after she adopted son David Banda — Madonna embraced motherhood again, only this time as a single mom. She added a fourth child to her brood: daughter Mercy James, whom she also adopted from Malawi. (The mother-daughter duo is pictured during a visit to the Gumulira Millenium villages in Mchinji, Malawi, the following year.)

Madonna won her second Golden Globe in 2012 for writing the original song "Masterpiece" from "W.E.," her sophomore directorial effort. (She first directed the 2008 comedy "Filth and Wisdom.") The historical drama centers around two love stories: the romance between the former King Edward VIII and divorcée Wallis Simpson and the burgeoning attraction between a New York City housewife and a new man. The film also earned a Golden Globe nomination (best original motion picture score) and an Oscar nomination (best costume design).

Madonna dabbled in dating a few more younger men following her divorce from Guy Ritchie, including model Jesus Luz and dancer Brahim Zaibat (pictured), who's 30 years her junior. Brahim accompanied Madonna on her successful MDMA world tour in 2012, but by late 2013, their relationship of three years had run its course.

A 55-year-old Madonna rocked lingerie during the 2013 Billboard Music Awards in Las Vegas, proving that age is only a number … and that shunning the sun and following a strict macrobiotic diet absent of sugar, wheat, eggs, meats and dairy clearly does a body good! (She also won three awards that night.)

Madonna gave longtime fans a glimmer of nostalgic hope that perhaps she'd found love once again with ex-husband Sean Penn when they were photographed at an art exhibit together in 2013, but sadly, a reconciliation wasn't in the cards. Although an eyewitness who saw him in the front row at her October 2013 "MDMA" concert in Los Angeles told Us Weekly he was saying, "She's so hot," while watching his ex perform — and despite pal Debi Mazar's' confession to Bravo's Andy Cohen that the actor was Madge's one true love — they were both linked to other people just months later: He started seeing Charlize Theron in late 2013 and she took her relationship with 26-year-old dancer-choreographer Timor Steffens to the next level in early 2014.

Madonna's much younger boyfriend, Timor Steffens, is seen here holding a car door open for her in Los Angeles on Jan. 29, 2014. Despite his chivalry, it wasn't meant to be: They called it quits in August 2014, just days before her 56th birthday. According to Us Weekly, the superstar asked the dancer to pack his bags and head home during the middle of their vacation in the South of France.

While there will never be another Madonna, a new generation of pop stars — including Miley Cyrus — have tried their best to follow in the Queen of Pop's controversial footsteps. Miley's dreams came true when Madge joined her onstage in January 2014 for her "Unplugged" special, during which they performed a mashup of "Don't Tell Me" and "We Can't Stop" – making Miley look good, and perhaps earning Madonna some cred with younger viewers. "It's nice when you work with someone who, like myself, doesn't really have anyone that you have to answer to," Miley told E! News.

Madonna caught everyone — including Drake! — off guard when she pulled him in for a kiss while making a surprise appearance during his headlining set as part of the 2015 Coachella Valley Music and Arts Festival. "Don't misinterpret my shock!! I got to make out with the queen Madonna and I feel 100 about that forever," he wrote on Instagram after the lip-lock made headlines. About a month later, Madonna opened up about the kiss and didn't have great things to say: "I kissed a girl, and I liked it," she said. Meow!

Madonna's Rebel World Tour kicked off in Canada in September 2015 and concluded in Australia in the spring of 2016. She performed more than 160 shows and brought in almost $170 million in revenue, making it a massive success.

Madonna and her sons, David Banda and Rocco Ritche, are seen here arriving at JFK International Airport in New York City on Jan. 7, 2015. The following year, things took a dramatic turn for the superstar when Rocco decided that instead of living with his mom in the United States, he wanted to live with his dad, director Guy Ritchie, in England. It took the former spouses nine months to iron out a custody agreement for Rocco, who turned 16 in August 2016. Adding to the drama, the teen got busted for marijuana possession in London that September. Fortunately, Madonna's relationship with her older son has improved dramatically since then.

Madonna's daughter, Lourdes Leon, joined her in the front row at the Alexander Wang presentation during New York Fashion Week on Sept. 10, 2016. The mother-daughter duo have shared a love for all things fashion since 2010, when they launched their Material Girl clothing line together.

In February 2017, Madonna announced that she'd adopted orphan twin girls — Stella and Estere — from Malawi. Six months later, she kept close to her new additions while traveling through JFK International Airport in New York City after a family vacation to celebrate her 59th birthday in Italy.

In July 2017, Madonna shared an embrace with daughter Mercy James at the opening of the Mercy James Institute for Pediatric Surgery and Intensive Care at the Queen Central Hospital in Blantyre, Malawi. The children's hospital was funded by the singer's Raising Malawi charity and is the first center of its kind in Malawi.

In the summer of 2017, Madonna and the underage members of her brood moved to Portugal so that her son David Banda could pursue his dream of becoming a professional soccer player. ("I've been desperate to get him into the best academies with the best coaches, but the level of football in America is much lower than the rest of the world. I saw his frustration, and I also felt it was a good time," she told Vogue Italia in 2018.) Not long after the big move, the superstar took her son to watch the FIFA World Cup Qualifier between Portugal and Switzerland at Luz Stadium in Lisbon on Oct. 10, 2017.

Madonna made waves with her eccentric ensemble during the 2018 MTV VMAs in New York City on Aug. 20 — just four days after she turned 60. She celebrated with an epic bash in Morocco.

Madonna introduced the world to her eye patch-sporting alter ego, Madame X, during the 2019 Billboard Music Awards on May 1. The following month, she dropped her "Madame X" album. That September, she hit the road on her "Madame X" tour, which kicked off in New York City and concluded in Paris in March 2020. A concert film chronicling the tour — the documentary is also called "Madame X" — debuted on Paramount+ on Oct. 8, 2021.

Madonna and her boyfriend of several years, dancer Ahlamalik Williams, made their red carpet debut as a couple at the premiere of her concert film "Madame X" in New York City on Sept. 13, 2021. The pair have grown incredibly close since they were first linked in 2018 — in spite of their age difference of 36 years. (Madge hasn't posed on the red carpet with a love interest since her marriage to filmmaker Guy Ritchie came to an end in 2008.)

Madonna showcases yet another side of herself in her new documentary, "Madame X," which chronicles her eponymous European and North American tour in support of her 2019 album of the same name and her eponymous eye patch-sporting alter ego — whom she's described as a globe-trotting secret agent who "changes her identity," "sleeps with one eye open" and "travels through the day with one eye shut." The concert film debuted on Paramount+ and on MTV on Oct. 8, 2021.