From Her Nearly Nude 'Vanity Fair' Shoot to All That Twerking: Miley Cyrus' Wildest Moments

The former child star turned grown-up songstress had her fair share of headline-making, head-scratching moments — here are the most memorable

USA - The 2015 MTV Video Music Awards - Arrivals
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Miley Cyrus is starting a new chapter.

Not only has the singer debuted a new, more mellow single called “Malibu” — a loved-up ode to fiancé Liam Hemsworth, whom she reunited with in 2016 — Cyrus also gave a revealing interview to Billboard, sharing that she’s “completely clean” when speaking of her past drug and alcohol use.

Though Cyrus has definitely gone through changes since releasing her 2015 album, Miley Cyrus and the Dead Petz, it’s been a wild ride to get there — emphasis on the wild.

Here, take a look back at the moments that grabbed the world’s attention (and dropped some jaws in the process) over the years.

1. Her Vanity Fair photoshoot.

At the height of her Hannah Montana fame in 2008, 15-year-old Cyrus shocked her fans (and their parents) when she posed semi-nude for Vanity Fair, posing with nothing more than a white sheet. The backlash was quick, with many parents of kids who looked up to Cyrus worrying about her decision to star in the photoshoot.

Cyrus then released a statement responding to the controversy, saying she didn’t initially understand how the Annie Leibovitz-shot photographs would look in their final form. “I took part in a photoshoot that was supposed to be ‘artistic’ and now, seeing the photographs and reading the story, I feel so embarrassed,” she said. “I never intended for any of this to happen and I apologize to my fans who I care so deeply about.”

2. Her 2009 Teen Choice Awards performance.

Or rather, dancing near a pole. For a performance of her hit “Party in the USA” at the Teen Choice Awards in 2009, Cyrus used a pole as a prop. Though the dancing was relatively tame, and mostly involved Cyrus gripping the pole, not gyrating against it, the implication was enough to cause a stir.

3. Her ‘Can’t Be Tamed’ music video.

The pole was just the beginning. In the music video for her 2010 song, “Can’t Be Tamed,” Cyrus dressed up like a rare bird and danced in a cage while a group of people ogled and took pics of the star.

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5. Her stoner admission.

While Cyrus has been candid about her marijuana use in recent years, the singer made big news in 2010 when she was caught on camera taking a hit of psychedelic salvia. Cyrus later apologized for the footage in an interview with Marie Claire. “I made a mistake,” she said. “I’m disappointed in myself for disappointing my fans. For me it was a bad decision, because of my fans and because of what I stand for.” In 2013, she sang a different tune in an interview with Rolling Stone, saying “As long as [marijuana] isn’t illegal, there are far more dangerous things. And it’s legal in the state of California. So I’m happy to live in California, a place where you can be whoever you want to be.”

6. Her engagement to Liam Hemsworth — at 19 years old.

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This moment was less wild than it was surprising — mostly because of Cyrus’s age. In 2012, at 19 years old, she confirmed her engagement to her Last Song co-star. Of course, we now know that the couple ended up calling things off in September 2013 after three years together — and then got back together in 2016.

7. Her 2013 MTV Video Music Awards twerk-fest with Robin Thicke.

One of the rumored reasons for her split from Hemsworth was her eyebrow-raising, tongue-wagging (literally) performance at the 2013 VMAs. After singing her song, “We Can’t Stop”, she performed “Blurred Lines” alongside Robin Thicke. The songstress wore a nude latex bikini and twerked on Thicke.

8. Her ‘Wrecking Ball’ video

The twerking on the VMAs stage was just the beginning. That same year, Cyrus debuted her music video for the song “Wrecking Ball” in which she swung on a — you guessed it — wrecking ball while naked (except for a pair of boots.)

9. Her on-stage moment with a Bill Clinton impersonator.

On her Bangerz tour, Cyrus had her backup dancers dress up as various American icons during her performance of “Party in the USA,” which included twerking with the Liberty Bell, dancing with Mount Rushmore and the Statue of Liberty, and pretending to perform oral sex on a dancer dressed as former President Bill Clinton.

10. Her 2015 VMAs hosting gig.

Two years after her now-infamous VMAs performance, Cyrus nabbed the show’s hosting gig in 2015. Throughout the entire night, she wore nearly-naked outfit after nearly-naked outfit, and even got in an on-stage spat with Nicki Minaj.

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