Miley Cyrus' Most Controversial Moments

Vanity Fair Photoshoot

Miley Cyrus courted controversy in 2008 when she was photographed topless for Vanity Fair by iconic shutterbug Annie Leibovitz.

'Asian Eyes' Photo

Cyrus was accused of mocking Asians by making slant-eye poses in a photo with friends that circulated online in 2009. Cyrus later wrote in a posting on her fan site that she wasn't making fun of any ethnicity but was simply making a goofy face.

Pole-Dancing 'Teen Choice Awards' Performance

Then-16-year-old Cyrus ignited controversy again when she performed her hit "Party in the U.S.A." at the 2009 Teen Choice Awards while writhing up and down against a stripper pole on top of an ice-cream cart.

Smoking Salvia

In 2010, Cyrus celebrated her 18th birthday by experimenting with a bong. While it looked like she was smoking marijuana, sources said the "We Can't Stop" singer was actually trying a natural herb called salvia.

'Can't Be Tamed' Music Video

The singer released the single "Can't Be Tamed" in 2010, expressing her need to break out and be free through the song. The music video, directed by Robert Hales, shows Cyrus as an exotic bird escaping from a giant cage.

Self-Proclaimed Stoner

In 2011, the singer, who celebrated her 19th birthday with a Bob Marley cake, said in comments caught on video, "You know you're a stoner when your friends make you a Bob Marley cake."

Engaged at 19

In 2012, the then-19-year-old Cyrus announced her engagement to Hunger Games actor Liam Hemsworth with a tweet that also said, "life is beautiful." The couple have experienced an on-again, off-again relationship since first meeting on the set of 2009 film The Last Song.

Twerking Photo

Cyrus tweeted this photo of herself mid-twerk earlier this year. Her dance moves would later show up in the video for "We Can't Stop" and her VMA performance.

'We Can't Stop' Music Video

This summer Cyrus showed she was no longer the squeaky-clean Disney star from Hannah Montana as she stripped down to crop tops and bodysuits and danced with giant teddy bears.

2013 MTV VMA Performance

Cyrus ignited a Twitter frenzy when she performed a racy version of her hit "We Can't Stop" and accompanied Robin Thicke on a duet of "Blurred Lines" at the 2013 MTV Video Music Awards. Wearing a furry bustier, Cyrus twerked, grinded, grabbed the rear end of one of her dancers, and touched herself and Thicke suggestively with a foam finger.

Posing for V Magazine

Cyrus sported an edgy punk-rock look on the cover of V Magazine earlier this year. The Mario Testino-shot cover features her wearing a pair of black-and-white underwear and a suit jacket without a bra.