Madonna's Most Iconic Photos Over the Years
Happy birthday to the Queen of Pop! It’s Madonna‘s 66th birthday today and this multi-hyphenate star has been serving up show-stopping pop culture moments for decades, wowing year after year on stage, at awards shows, and even from the comfort of her home as she’s taken on social media by storm.
It’s hard to keep track of the many lives Madonna has lived, from her roles in films like Evita and A League of Their Own to her industry-shaking 14 albums and seven Grammy wins, all while developing an international reputation for her style and status as a sex symbol. Every time you think you know Madonna, she reinvents herself — and we’re looking back on the many eras of Madonna with this collection of truly iconic photos.
There’s Madonna today, a loving mother of six and nonprofit founder; there’s “Like a Virgin” Madonna, making jaws drop everywhere at the 1984 VMAs — and of course, kissing-Britney-Spears Madonna, at the same show nearly 20 years later. At the Billboard Women in Music Awards in 2016, Madonna looked out at the crowd of her peers, reflected on her long legacy, and said: “I think the most controversial thing I have ever done is to stick around,” she said, per The New York Times. She has always been a woman who controls how she is looked at, and the proof is clear: even now, none of us can look away.
Take a look at some of Madonna’s most iconic moments so far captured below.
A version of this article was originally posted on Aug. 2021.
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Dancer Headshots (1978)
Before her big break, Madonna moved to New York City to study dance and the photos are hypnotizing.
London (1983)
Everyone was captivated by Madonna’s outfits and onstage presence, especially during this show in 1983.
Madison Square Garden (1984)
When Madonna performed onstage at Madison Square Garden in 1984, all eyes were on the entertaining wild child.
American Music Awards (1985)
Who remembers this Madonna? The slicked-back bangs, the side pony, and the ever-present cross necklace already making a big appearance.
Blond Ambition World Tour (1990)
All hail the Gaultier cone bra! Madonna invented the look, rocking these pointy bits of lingerie all across America and the world.
Academy Awards After Party (1991)
While Michael Jackson and Madonna didn’t even officially date, the pop stars had a one-time date to none other than the 1991 Oscars.
“Michael [Jackson] was like, ‘Well, who are you going to go with?’” Madonna said in a VH1 interview. “I looked at him and said, ‘I don’t know. You want to go?’ And he said, ‘Yeah, that’d be great.’ … And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you.”
In a 2016 appearance on James Corden’s Carpool Karaoke, the singer was asked if she kissed the Prince of Pop and responded: “Of course. I mean, baby, I’ve been around.”
Cannes Film Festival (1991)
Madonna dressed up her iconic cone bra for the carpet at the Cannes Film Festival premiere of In Bed With Madonna. The briefs-inspired shorts and hot pink coat were quite a statement.
Sanremo Music Festival (1995)
Madonna and Babyface performed at the 45th Sanremo Music Festival in 1995. The pair sang “Take a Bow,” which afterward, Madonna thanked everyone in Italian, receiving a standing ovation.
‘Evita’ Premiere (1996)
Madonna played Eva Perón in Alan Parker’s Evita, and her hotly-anticipated arrival at the Los Angeles premiere was well worth the wait when she rolled up in this scarlet Givenchy. “I feel like Cinderella,” Madonna told CNN as she arrived to director Parker and co-star Antonio Banderas.
MTV Video Music Awards (1998)
In 1998, Madonna and Jonas ?kerlund (pictured) cleaned up big at the VMAs, with their video for “Ray of Light” taking home a record five awards.
‘Die Another Day’ Premiere (2002)
Madonna was technically here to see Pierce Brosnan and Halle Berry’s James Bond film Die Another Day — but, more realistically, she was there to curtsy and shake the hand of the late Queen Elizabeth II.
MTV Video Music Awards (2003)
Just in case her “Like A Virgin” performance at the VMAs years prior hadn’t shattered enough TV screens, Madonna shared this unforgettable kiss with Britney Spears (and another with Christina Aguilera!) in 2003.
“It was just a friendly kiss!” Madonna said of the moment in an interview with Oprah. “It was totally meant in innocence and I don’t know why people are making such a big deal about it. Hasn’t anyone else seen two girls kiss before?”
‘Revolver’ Screening (2005)
Madonna and Guy Ritchie, pictured here in 2005, were married from 2000 until their divorce in 2008.
While they eventually ended things, the beginning of their love story was quite remarkable. A few months into their relationship,in March 2000, announced they were expecting a baby. Ritchie and Madonna’s son Rocco Ritchie was born on August 11, 2000. Their wedding followed on December 22 at Skibo Castle in Scotland.
In 2006, they adopted their son David Banda from Malawi, but their marriage only survived another two years. They announced their divorce in October 2008.
Madonna later reflected on their marriage in a 2017 interview with Newsweek. “When you start off, everything’s great and lovely, and the person you’ve married is flawless, and you’re flawless,” she said. “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.”
Vanity Fair Oscars Party (2006)
Madonna attended the 2006 Vanity Fair Oscars party in this silk Versace gown that has lived in our minds rent-free since.
Vanity Fair Oscars Party (2007)
After the 2007 Academy Awards, Madonna headed to the after-party at Mortons in her black Dolce & Gabbana gown.
Met Gala (2009)
The 2009 Met Gala theme was “The Model as Muse: Embodying Fashion,” and here’s Madonna in Louis Vuitton doing just that.
Vanity Fair Oscars Party (2009)
In 2009, Madonna’s after-party plans took her to the Sunset Tower Hotel in a glittering Christian Dior dress.
Met Gala (2011)
Madonna went with this blue Stella McCartney look for the 2011 Met Gala, themed “Alexander McQueen: Savage Beauty.”
Golden Globe Awards (2012)
Madonna won Best Song at this year’s Golden Globes for “Masterpiece” in the soundtrack of W.E., and looked stunning in this Reem Acra gown.
‘Madonna: The MDNA Tour’ Premiere (2013)
Madonna channeled Marlene Dietrich in full force for the premiere of her ninth concert tour.
Met Gala (2013)
They asked Madonna to dress for ‘Punk: Chaos to Couture’ — do you think this Givenchy look did the trick?
Met Gala (2016)
In celebration of the opening of ‘Manus x Machina: Fashion in an Age of Technology’, Madonna showed off her curves in this black lace Givenchy number.
Met Gala (2018)
For ‘Heavenly Bodies: Fashion and the Catholic Imagination’, it truly seemed like Madonna had been preparing her whole life. Her Jean-Paul Gaultier get-up did not disappoint — and neither did her surprise performances of “Like A Prayer” and “Hallelujah” for enthralled guests.
Pride Island (2019)
Madonna showed her pride as she wore this iconic rainbow and black outfit onstage during Pride Island in 2019!
MTV Video Music Awards (2021)
Who could forget Madonna’s outfit and speech at the MTV Video Music Awards in 2021?
Burberry Event (2022)
Madonna rocked her iconic all-black look, looking like edgy royalty at the Burberry Lola bag celebration in April 2022.
65th Grammy Awards (2023)
Madonna looked confident from head to toe as she presented during the 65th Grammy Awards earlier this year. The twisted braids and ultra-high slit really make the look!
The Celebration Tour (2023)
Madonna proved her latest tour, The Celebration Tour, was a total family affair back in October 2023. To celebrate the beginning of the tour, the “Material Girl” singer was joined by her kids Estere and Stella Ciccone, 11, Mercy James, 17, David Banda, 18, and Lourdes Leon, 27 onstage. Her eldest son Rocco Ritchie, 23, was just nearby admiring!
Among the performances that night was Estere captivating fans with her ballroom-inspired runway, Stella performing Madonna’s Western-inspired song “Don’t Tell Me,” Mercy playing the piano to “Bad Girl” and David playing guitar during “Let’s Go Crazy” and “Mother and Father.” Lourdes also joined her mom onstage to celebrate Estere’s incredible performance.
‘Deadpool & Wolverine’ Premiere (2024)
Madonna proved to be the coolest mom ever as she brought her twin daughters Estere and Stella to the Deadpool & Wolverine World Premiere on July 22, 2024, in New York City. A VIP look into one of the year’s biggest movies and a meet-and-greet with Ryan Reynolds and Hugh Jackman? Count us in!
