Pop quiz: who do you think about when you read the phrase “scandalous singer?” These days, you might think of Kanye West, a star whose antics seem to get crazier by the minute. The best answer, though, is Madonna. This self-styled Queen of Pop was a controversy magnet long before Kanye hit the scene, and she still continues to ruffle feathers in the present day.
In fact, the “Like A Virgin” singer has had so many scandalous moments that it’s tough to pick out the one that shocks us the most. Nonetheless, we decided to sift through the singer’s sordid history to bring you the best (or maybe that should be the worst) of her musical misadventures.
Ready to relive the wildest moments of the most shocking star in musical history? Keep reading to discover the biggest scandals of Madonna, the once and forever Queen of Pop.
Madonna’s disastrous appearance on David Letterman
For fans of late-night television, Madonna’s biggest scandal didn’t come from an appearance on MTV…instead, it came from an appearance on David Letterman! In 1994, the singer appeared on his late-night show for what was meant to be a relatively chill interview. But when a member of the audience requested to kiss the musician and Letterman encouraged her to say “yes,” the entire interview soon turned into a lopsided disaster.
Arguably, this all started with Madonna telling Letterman, “I can’t. Why are you so obsessed with my sex life? You’re a pervert.” This caused the Letterman-loving audience to freak out, but this didn’t keep the musician from tearing the host a new one across 20 agonizing minutes. By the time it was over, she had said the f-word a whopping 13 times, making television history in the most scandalous possible way.
Her same-sex kiss with Britney Spears and Christina Aguilera
Remember when we said that Madonna has always courted scandal? In 2003, less than a decade after her wild interview with David Letterman, Madonna performed at the MTV VMAs. She wasn’t alone, though, performing alongside major pop icons Britney Spears and Christina Aguilera. While the musical performance was awesome, what made this appearance scandalous is what happened after the song: an unexpected pair of same-sex kisses!
You see, Madonna has never been shy about showing affection or courting controversy. And she combined both of those traits into a jaw-dropping moment where she kissed both of the women that she had been performing with. The moment shocked the world, but perhaps nobody was more shocked than Justin Timberlake. In fact, cameras captured the moment that he couldn’t stop staring at pop legend Madonna locking lips with Britney Spears, his famous ex and a musical icon in her own right.