It’s easy to be dismissive of celebrities who are famous for acting wild. After all, we can’t help but wonder whether celebs who dominate tabloid headlines have any talent or just like to cause trouble. However, there are also some insanely talented celebs out there whose ability to cause trouble is only outmatched by their sheer talent.
The best example of this is Miley Cyrus. Early on, the singer managed to shed her reputation as a Disney Channel princess with one scandal after another. But these scandals never really derailed her career, and if anything, Cyrus has only gotten better at singing across a decade of crazy headlines.
Just how crazy are we talking? We’ve got you covered. Keep reading to discover the wildest Miley Cyrus moments ever caught on camera!
Posing topless
The very idea of an underage girl posing topless for a major magazine is downright scandalous. Nonetheless, that’s exactly what Miley Cyrus did in 2008. She was only 15 years old at the time, but this didn’t keep her from posing topless (sort of) for Vanity Fair.
To be clear, she didn’t show any nudity in these photos. Instead, these images from legendary photographer Annie Leibovitz portrayed Cyrus with an exposed back, wrapped in nothing but a sheet. She had red lipstick, artfully tousled hair, and an impish sense of humor.
The photos are beautiful, and they pale in comparison to the naughty things that would leak later. At the time, though, seeing this Disney Channel icon topless in a major magazine helped Cyrus start shedding her reputation as America’s girl next door.
Naughty leaked image
That same year, we got to see far more of Miley Cyrus than she showed off in Vanity Fair. In 2008, the singer was hacked and some of her photos were leaked online. This included intimate photos of herself that she had taken for her then-boyfriend Joe Jonas.
Once again, these photos were not nude. But they did show the underage Disney Channel star in a bikini, crop top, and even a wet t-shirt. Such risque photos implied that she and Jonas were enjoying a sexual relationship. That’s perfectly normal for teens their age, but both Cyrus and Jonas had made a big deal of sporting matching purity rings; accordingly, the release of these saucy photos made many accuse these young stars of hypocrisy.
Taking potshots at fellow Disney stars
Obviously, Miley Cyrus couldn’t help getting hacked and having her private photos released online. Sometimes, though, she lands in scandals that are completely her own fault. The worst example of this is when the singer and Mandy Jiroux posted a video on YouTube that trashed Disney Channel’s newest stars: Demi Lovato and Selena Gomez.
This shocked the world because, frankly, everyone thought that Cyrus would team up with Lovato and Gomez, welcoming these new gals on the block into the fold. So much for girl power, though, as Cyrus wasted no time dragging these two new girls for filth in a highly public way.
The backlash against Cyrus was almost instantaneous. Later, the singer took the video down and apologized, though she maintained that she and Jiroux were simply trying to be funny.
The 2013 VMAs: Miley’s Cultural Earthquake
At the 2013 MTV Video Music Awards, Miley Cyrus ditched her Disney roots with a performance that stunned the world. Dressed in a nude-colored latex two-piece and rocking playful space buns, she launched into a wild rendition of “We Can’t Stop” before joining Robin Thicke for “Blurred Lines.”
Armed with a giant foam finger, Miley twerked, grabbed, and gyrated in ways that left jaws on the floor. The moment she bent over and twerked on Thicke became an instant viral sensation, sparking a cultural firestorm. Memes flooded the internet, news outlets exploded with commentary, and “twerking” was officially part of the pop lexicon.
The backlash was fierce—accusations of indecency and cultural appropriation swirled—but Miley didn’t flinch. Instead, she cemented her transformation from child star to fearless provocateur, making it clear: Hannah Montana was gone for good.
Wrecking Ball: Naked and Unapologetic
When Miley Cyrus released the “Wrecking Ball” music video in 2013, she didn’t just drop a breakup ballad—she detonated a pop culture bomb. Directed by Terry Richardson, the video featured Miley swinging naked on an actual wrecking ball, her vulnerability exposed both emotionally and physically. It was a stark contrast to the glossy pop stars of the time—and a direct challenge to her critics.
The imagery was raw, jarring, and unforgettable: Miley in boots and nothing else, clutching the wrecking ball while singing about heartbreak and destruction. She also licked a sledgehammer and stared down the camera with tear-filled eyes, mixing sensuality with pain in a way that made audiences uncomfortable—and unable to look away.
The video racked up millions of views within hours and drew fierce backlash and praise alike. Some saw it as a desperate cry for attention, others as a bold artistic reinvention. Either way, it worked—“Wrecking Ball” became one of her biggest hits, and the visual became a symbol of Miley’s complete break from her innocent past.
Burning the Rulebook at Glastonbury
Miley Cyrus took the stage at the 2019 Glastonbury Festival and immediately made it clear—this wasn’t your typical pop princess set. Dressed in black leather, fishnets, and oversized sunglasses, she looked more like a post-apocalyptic rock star than a Top 40 chart-topper. Her vibe? Unfiltered, raw, and ready to ignite chaos.
She tore through a gritty setlist that mashed up her biggest hits with rock-infused covers, including a surprise rendition of Nine Inch Nails’ “Head Like a Hole.” Profanity flew, energy spiked, and the crowd roared as she threw herself into every note like she had something to prove—and nothing to lose.
More than just a performance, it was a declaration. Miley wasn’t following the rules—she was rewriting them. By the end of the set, she hadn’t just entertained a field full of fans—she’d reminded the world that she can’t be boxed in, labeled, or tamed.