Miley Cyrus' Most Outrageous Moments

Once a poster child for family programming, Miley Cyrus has been held to an impossibly high standard for most of her career. The former Hannah Montana star hasn't always lived up to the squeaky-clean image expected of Disney stars, however, proving herself quite human with a number of controversies in her 19 years.

Here's a rundown of Miley's most outrageous moments.

Miley's best bikini duckface, circa 2007. (Bauer Griffin) The Duckface Photos
Miley's first brush with scandal came in late 2007, when images posted on her private MySpace account and hacked from her Gmail inbox made the rounds on the Interwebs. What the public learned about Miley: She's prone to tacky self-portraits, like many a preening teenage girl. But she should have thought twice before snapping a photo of herself in her underwear and uploading it to the Web.

Cyrus apologized: "I am going to make mistakes and I am not perfect. I never intended for any of this to happen and I am truly sorry if I have disappointed anyone."

The "Topless" Shot
Most people who get their picture taken by famed photographer Annie Leibovitz leave honored. Then there's Miley Cyrus, who was forced to apologize after Vanity Fair published a shot of the then 15-year-old wrapped in a bedsheet in its June 2008 issue. Perhaps even creepier was a shot of Miley cuddling up to her Hannah Montana co-star, dad Billy Ray Cyrus.

Workin' the Pole
In September 2009, when Miley was 16, she performed her summer smash hit "Party in the U.S.A." at the Teen Choice Awards atop a faux ice cream cart outfitted with a helpful pole to slide down. The implications were not lost on mortified parents.

The fact that Miley was later videotaped giving director Adam Shankman a lap dance at a cast party for The Last Song didn't help matters. Miley's dad defended her choice of stage prop, shrugging, "I always tell her to love what you're doing and stay focused for the love of the art and not worry so much about opinion."

Little Miss Salvia
Miley had just turned 18 when she was videotaped taking deep hits from a bong and giggling uncontrollably with friends. Perhaps more shocking: They were listening to Bush when it went down.  Of course the video found its way to the web, and though Cyrus' reps were quick to note that the substance being inhaled was salvia, not marijuana, and therefore completely legal. The event had Cyrus' then-estranged father expressing his remorse via Twitter: "Sorry guys. I had no idea. Just saw this stuff for the first time myself. There is so much beyond my control right now."

Bob Miley
The Ghost of Bongs Past revisited Miley after her 19th birthday party, when footage of her reacting to a Bob Marley-decorated birthday cake was spread far and wide. Cyrus cracked, "You know you're a sntoner when your friends make you a Bob Marley cake. You know you smoke way too much f**kin' weed."

Miley's reps insisted the performer was only referring to an inside joke between her and pal Kelly Osbourne, who had taken to calling Cyrus "Bob Miley" in the wake of the salvia incident.

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Miley's controversial moments are kid's stuff compared to the other salacious stories in this juicy feature. See what rock 'n' roll legends are made of in our juicy new feature about music's most outrageous moments!