PHOTOSMadonnas's Wildest Moments Through Her Years Of Fame — See The Legendary Photos
April 27 2022, Published 1:05 p.m. ET
Never a dull moment!
Madonna has been keeping audiences entertained for decades, and her ability to raise eyebrows still never ceases to amaze her fans.
Since becoming a legend in the industry back in the 1980s, Madonna, 63, has lead a wildly successful music career jam-packed with both iconic and notorious moments.
To take a look back at her iconic career, OK! has rounded up some of the Queen of Pop's wildest and most legendary moments over the years.
Scroll through the images below to see our favorite Madonna moments:
She Appears On David Letterman In 1994
In 1994, Madonna appeared on on CBS' Late Show with David Letterman in now-infamous interview, where she said the f-word 14 times and even refused to leave the stage.
During the course of the interview, Madonna smoked a cigar and made multiple innuendos after walking on stage with a pair of her underwear, which she asked Letterman to smell.
She even called Letterman a "sick f**k," in the episode, which is has since become of the highest-rated of his career.
Her Oscars Appearance With Michael Jackson
Back in 1991, both the King and Queen of Pop made an iconic pair at the Oscars. Madonna asked Michael Jackson to be her plus one for the event, and the pair seemed to have quite the night together.
In an interview at the time, Madonna explained how the date came about, saying “Michael was like, ‘Well who are you gonna go with?’ I looked at him and said, ‘I don’t know. You wanna 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."
Her Tense Interview With Courtney Love
Madonna's famous feud with Courtney Love was on display at the 1995 VMAs. The "Like a Virgin" singer was being interviewed with MTV's Kurt Loder when she got a compact thrown at her by Love.
"Hi Courtney," Loder responded. "That's Courtney Love, everybody's favorite," before inviting her up to the stage, to Madonna's dismay.
"Courtney Love is in dire need of attention right now," she fired in the clip, per MTV, before Love joined them on stage for the rest of the very tense interview.
Her Famous Cone Bra
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Madonna's Blond Ambition tour in 1990 was the starting place for many of her most provocative and iconic outfits, including the famous Jean Paul Gaultier cone bra.
According to Dazed, Madonna personally sent a letter to Gaultier to request he design all of the costumes for the tour, with the conical bra taking months to create.
The legendary garment later sold for $52,000 at the Christie’s Pop Culture auction in London in 2012.
The Britney Spears Kiss
In 2003, Madonna took the VMA stage alongside Princess of Pop, Britney Spears, before the two blonde beauties engaged in an unforgettable kiss.
The onscreen moment has since become one of the most iconic moments in all of VMA history, as well as Justin Timberlake's unamused facial expression in reaction to the smooch.
Sex Book
Not only famous for her contributions to the music industry, Madonna also published a book in 1992, which ended up sparking major controversy.
The book titled Sex, featuring graphic sexual images, sold as a $50 coffee table book at the time and eventually made it to The New York Times Best Seller list.
Today, the book is still considered the "most radical career move" a popstar has ever made, according to Huffington Post.
Kisses Drake At Coachella
In 2015, Madonna once again made headlines after planting a surprise kiss on Drake during his set at the Coachella music festival.
After the intense makeout session, Drake famously looked disgusted, which wasn't exactly the reaction anybody was expecting.
But the rapper later clarified the situation, writing via Instagram: "Don't misinterpret my shock!! I got to make out with the queen Madonna and I feel 100 about that forever. Thank you @madonna," as Insider reported.
