Disney stars have a history of going through rebellious phases, oftentimes acting out in various acts of defiance in order to shed their heavily-monitored, squeaky-clean public personas set forth by their G-rated, Mickey ears-wearing Hand that Feeds.

Arguably the most potent of Disney rogues, Miley Cyrus has undergone perhaps one of the most drastic “coming of age” transformations pop culture has ever had the pleasure of bearing witness to. As the star of the popular children’s TV show Hannah Montana, Cyrus, with her Southern twang accent and infectious smile, was the parent-approved role model every child aspired to be.

Fast forward to the present, and the singer is making headlines of a different sort. Now a parent’s allegory for “Where did I go wrong?”, Miley’s transformation from dainty Disney princess to tongue-wagging twerk queen has made her subject to countless controversies, debates and tabloid covers.

Having hit full circle with her recent T&A-laden Terry Richardson spread for Candy Magazine, we look back at the singer’s career to provide you with 16 of her most controversial moments.

Myspace Mishaps

In 2008, a flurry of jailbait-luring photos of the then-squeaky clean Hannah Montana starlet seeped their way into cyberspace. The pics showed the singer in full-on Myspace-ready duck face poses while flaunting her midriff in bathrooms and Hello Kitty bedsheets. While the snaps pale in comparison to Miley’s current getups, they were still suggestive enough to warrant concern among parents and her impressionable tween fanbase.

'Vanity Fair' Cover

While it might seem modest, this 2008 Vanity Fair spread shot by renowned photographer Annie Leibovitz was perhaps one of the first of Miley’s controversies to cause a significant amount of widespread furor. The photos, one being a creepy mall-grade family portrait of Miley leaning against her father Billy Ray Cyrus, while the other pictured the 15-year-old posing topless beneath a satin wrap, outraged Disney execs, who stated, “For Miley Cyrus to be a ‘good girl’ is now a business decision for her. Parents have invested in her a godliness. If she violates that trust, she won’t get it back.”

The singer responded to the scandal with remorse, issuing the statement: “I took part in a photo shoot that was supposed to be 'artistic' and now, seeing the photographs and reading the story, I feel so embarrassed. I never intended for any of this to happen and I apologize to my fans who I care so deeply about," she said at the time.”

Teen Choice Awards Pole Dance

It turns out Miley has a history of ruffling peoples feathers during award show performances. Before she twerked the nation, Miley took her moves onto the stripper pole (still on Disney’s payroll, mind you) while performing her 2009 summer anthem “Party in the U.S.A.” at the Teen Choice Awards. After fans took to the internet to debate whether Cyrus' performance was too risqué for her age and young fanbase, the Mickey Mouse affiliates seemed eager to avoid being linked to the controversy. “Disney Channel won't be commenting on that performance," the network said in a statement, "although parents can rest assured that all content presented on the Disney Channel is age-appropriate for our audience - kids 6-14 - and consistent with what our brand values are.”

“Can’t Be Tamed” Era

A turning point from her Disney-monitored teeny popper image, 2010’s “Can’t Be Tamed” kickstarted Miley’s “rebellious” phase - something nearly every former Disney star goes through it seems. Billboarded by the album’s self-titled lead single, the song was accompanied by a sultry music video displaying a strong sexual appeal that wasn’t prevalent in the singer’s previous works. Exerting themes of freedom and self-expression, the era would lay to rest the Hannah Montana good girl the world once knew.

Salvia Scandal

OK, so here’s where things start going from slap on the wrist mishaps, to full-blown tabloid smut. In December 2010, a TMZ-watermarked video surfaced showing Miley ripping a bong and giggling while having “a little bit of a bad trip.” The ex-Disney star claimed that the inhaled substance was a hallucinogen called Salvia, which happens to be legal in the state of California. But nevertheless, the singer came clean on the controversy, telling Marie Claire: “It was a bad decision, because of my fans and because of what I stand for. I’m not perfect … I made a mistake. I’m disappointed in myself for disappointing my fans.”

Stoner Confession

During her 19th birthday in 2011, Cyrus came forth with the following confession: “You know you're a stoner when your friends make you a Bob Marley cake. You know you smoke way too much f**king weed!” Guess the Salvia wasn’t cutting it anymore.

Early Engagement

After maintaining a capricious relationship with Hunger Games actor Liam Hemsworth for over three years, Miley did what any other rational-thinking 19-year-old would do after going on-again, off-again steady - she got engaged. The two betrothed in early June of 2012 only to call it quits nearly a year later. Well, she can’t be tamed, after all.

Hair Today, Gone Tomorrow

Chopping off a signature do makes a loud statement in the entertainment industry. Rihanna and J Biebs both demonstrated significant transformations in personality and public image when they sliced off their luscious locks, and rest assured, Miley’s new look would follow suit. The singer decided to close 2012 by cutting her traditionally long, brown hair in favor of a bleached blonde, pixie-style haircut, exhorting on Twitter that she "Never felt more me in my whole life.”

“We Can’t Stop” Video

Released in June 2013, the visual accompaniment for the lead single from Miley’s fourth studio album Bangerz officially christened her Disney girl gone rogue image. The video for “We Can’t Stop,” a song which boasts “dancing with molly” and “trying to get a line [of cocaine] in the bathroom,” depicts a house party where weirdos and ravers thrive amidst a series of bizarre happenings including the construction of a white bread mountain, the kicking of a skull made of french fries and the simulated slicing of a woman's fingers. The clip was met with considerably mixed reviews; some lauding the singer’s newfound sexual liberation, others annoyed by her “desperate” attempts at being provocative.

The VMA Twerk That Shook the World

Further flexing her ratchet streak, Miley stirred up a media storm and garnered a significant amount of public scrutiny following her controversial performance at the 2013 MTV Video Music Awards. The spectacle began with a chronic tongue-rolling Cyrus performing “We Can’t Stop” in a teddybear onesie, following a “Blurred Lines” duet with Robin Thicke where she proceeded to strip down to a nude-colored two-piece latex outfit and infringe on the R&B singer’s personal space - which meant rubbing his groin area with a giant foam finger and twerking against his crotch.

The display was met with widespread criticism, with publications such as The Hollywood Reporter dubbing it as “crass” and “reminiscent of a bad acid trip” as well as (my personal favorite) a “trainwreck in the classic sense of the word as the audience reaction seemed to be a mix of confusion, dismay and horror in a cocktail of embarrassment,” as described by XXL critic B. J. Steiner. The performance - which became the most tweeted about event in history since Beyoncé's Super Bowl XLVII halftime show - was also accused of contributing towards the dehumanization of black women by mimicking "ratchet culture" and using them as living props, to which the singer replied: “They're overthinking it. You're thinking about it more than I thought about it when I did it.”

“Wrecking Ball” Video

Marking one of the first glorious collaborations with fashion’s leading raunch jock photographer Terry Richardson, Miley - whose iron was still hot from that eye-popping VMA twerkfest - caused heads turning yet again with the provocative video for her Bangerz-featured single “Wrecking Ball.” Directed by Richardson, the (naturally) perverse visual depicted a nude Cyrus swinging on a wrecking ball and fellating a sledgehammer - all while looking unsettlingly underage and vulnerable.

Terry, Tongue-Rolling & Arizona Iced Tea

When the newly-formed gruesome twosome joined forces during an NYC visit, they thought how better else to spend their precious time together than snap some salacious photos posing half-nude in a hotel room while groping a can of Arizona Iced Tea? While the semi-pornographic pics continued to ruffle feathers - something that became Miley’s schtick at this point - reps at Arizona Iced Tea gave their seal of approval, stating: “Nothing but sales will come in the long run from you holding one of our cans of delicious AriZona Iced Tea like a big, hard cock and it is absolutely NOT in ANY way costing us anything for this advertising.”

Blazed Up Acceptance Speeches

So thus far, we’ve established that Miley is both A) fond of ganja and B) a media troll. So put two and two together, and you get the singer lighting up a joint onstage while accepting the Best Video accolade for her song “Wrecking Ball” at the 2013 MTV Europe Music Awards, which she justified with the statement, “I couldn't fit this award in my purse but I did find this.”

Homeless Convict VMA Date

Making yet another bold statement at a VMA ceremony, Miley continued to dominate headlines when she was accompanied by a homeless man named Jesse Helt at MTV’s 2014 show. Helt was thrown into the spotlight when he accepted Miley's MTV Video Music Award for Video of the Year for "Wrecking Ball,” a move that was meant to encourage musicians to learn more about homeless youth in Los Angeles. It was soon later discovered that Miley’s date was arrested on charges of criminal mischief and criminal trespass and was given a six-month jail sentence for violating his probation.

Miley Vs. Nicki Minaj

Returning to yet another VMA show debacle, this year’s show welcomed a very public feud between the rogue pop star and hip-hop’s leading lady Nicki Minaj. Given her history with the ceremony, MTV thought who better to host their 2015 event than the ex-twerk queen. But even before the show kicked off, there was an ongoing tiff between Cyrus and Minaj over the rapper’s sour reaction to not being nominated for the Video of the Year category. “You made it about you. Not to sound like a bitch, but that’s like, ‘Eh, I didn’t get my VMA’…If you want to make it about race, there’s a way you could do that. But don’t make it just about yourself,” Miley stated in a New York Times interview.

Needless to say, the hot-tempered “Anaconda” emcee didn’t take the criticism lightly and publicly called her out after accepting Best Hip Hop Video award. Miley, in turn, claimed the media manipulated her words and then snidely congratulated Nicki for winning. And this was after the singer posted a pre-show photo of herself in her birthday suit on Instagram.

'Candy Magazine' Spread

Alas, we come to a close by presenting you with this tasteful photo shoot of the starlet coming full circle. Featuring a few familiar tropes - Terry Richardson, exposed tongue, violating inanimate objects - this Candy Magazine shoot marks perhaps the most NSFW shoot to date (she had to top herself somehow) and features the artist posing naked with a cat, dressing up as a man of the law and frisking with a strap-on. Not surprising at this point, but it makes you wonder: “What will Miley do next?”

Check out more from our Most Controversial series by clicking the following:

20 Controversial Ads That Defined American Apparel (NSFW) 10 of the Most Controversial Fast-Fashion Shirts Ever (NSFW) 10 of the Most Controversial Fashion Photographers Ever (NSFW) Jeremy Scott’s 5 Most Controversial Moments 10 Controversial Film Directors Every Highsnobiety Reader Should Know 15 of the Most Controversial Movie Posters of All Time (NSFW) 8 of the Most Controversial Hip-Hop Album Covers of All Time (NSFW) 10 of the Most Controversial Fashion Ads of All Time (NSFW)

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