1. Demi Lovato
While she got her start as a kid on Barney & Friends, Demi Lovato became a Disney star when she landed the lead role in the Jonas Brothers movie Camp Rock. She soon got her own Disney sitcom, Sonny With a Chance.
Lovato began appearing in the tabloids in 2010 after punching a back-up dancer and entering a treatment facility for issues that included bulimia, self-harm, and drug and alcohol abuse. Since her recovery, she’s focused more on her music. In 2012, she became one of the new hosts of The X Factor.
2. Miley Cyrus
The daughter of country star Billy Ray Cyrus, Miley first stepped into the title role of Hannah Montana in 2006. The show was a huge success, spawning soundtracks and films, including the concert film Hannah Montana and Miley Cyrus: The Best of Both Worlds and Hannah Montana: The Movie.
“I’m sorry I’m not perfect,” Miley has said following controversies including a photo of her smoking salvia from a bong, a pole dance at the Teen Choice Awards, and her assertion that a Bob Marley-themed birthday cake means “you know you smoke way too much fuckin’ weed.” She’s also taken on more adult roles in films like The Last Song and LOL.
3. Vanessa Hudgens
Although Vanessa Hudgens had a small role in the dark drama Thirteen, she achieved fame as sweet Gabriella Montez in High School Musical. The smash hit prompted two sequels, including High School Musical 3, the first to premiere in theaters instead of on the Disney Channel.
Since the conclusion of the High School Musical series, Hudgens has gone for mature roles, most recently playing the twisted Candy in Spring Breakers. She was also the victim of nude photo hacking, which some speculated would force Disney to drop her entirely. They didn’t.
4. Zac Efron
Vanessa Hudgens’ High School Musical co-star Zac Efron didn’t even sing his own songs in the first film. Rest assured he got full vocal duties in High School Musical 2 and High School Musical 3, which helped cement his standing as a teen heartthrob.
If you want to see Efron in his underwear a lot, check out The Paperboy. That’s likely the film that removed any lingering feelings of Disney wholesomeness, although dropping a condom on the red carpet didn’t hurt. Efron is also playing adult leads now, as in the Nicholas Sparks movie The Lucky One.
5. Selena Gomez
Selena Gomez has serious Disney credits: she guested on The Suite Life of Zack & Cody before taking on a recurring role on Hannah Montana. In 2007, she was cast as Alex Russo on The Wizards of Waverly Place. The series was such a big hit that Gomez was quickly hailed as “the next Miley Cyrus.”
Gomez started her own band, Selena Gomez & The Scene, which put out three albums. Her film roles have been mostly Disney-friendly, except for her latest. Gomez stars in Spring Breakers alongside fellow Disney alum Vanessa Hudgens: it’s heavy on the sex and drugs.
6. Ashley Tisdale
As brat-with-a-heart-of-gold Sharpay, Ashley Tisdale was another one of the High School Musical break-outs. She went on to star in the sequels and her own spin-off film. But before that, Tisdale played a much nicer character in the Disney Channel series The Suite Life of Zack & Cody.
Tisdale put it pretty simply when she posted nude for Allure in 2011: “I’m not just the young girl everybody thinks I am. I’m actually a woman.” She also picked more mature roles, transitioning from Disney to the CW. Most recently, she played Emma Jean on the gritty FX drama Sons of Anarchy.
7. Corbin Bleu
Although he never reached Zac Efron’s level of success, Corbin Bleu had plenty of fans after playing Chad Danforth in the High School Musical movies. Bleu also had a role on Hannah Montana and starred in the Disney Channel Original Movie Jump In!
As a grown-up, Bleu has had guest spots on The Good Wife and Blue Bloods. Like other Disney stars before him, he made the switch to the CW playing a male model on TBL: The Beautiful Life, which was quickly canceled. He also stepped things up vocally when he starred in In the Heights on Broadway.
8. Aly Michalka
Disney actually gave Aly Michalka her first role with Phil of the Future, on which she played Keely Teslow. She went on to star in two Disney Channel Original Movies, Now You See It… and Cow Belles.
After appearing in Bandslam alongside Vanessa Hudgens, Michalka went after edgier roles in films like The Roommate and Easy A. In the latter, she’s Olive’s sexpot best friend Rhi. In her personal life, Michalka has remained mostly under the radar.
9. Hilary Duff
In 2001, Hilary Duff took on the title role in Lizzie McGuire, one of the first Disney Channel series to propel its lead to teen stardom. She was also in the Disney Channel Original Movie Cadet Kelly in 2002, and Lizzie McGuire The Movie in 2003.
Duff is married — and a mom! But before that, she was working to move past her child star past. Her music began to carry a sexier image, which some found jarring in relation to her Lizzie McGuire role. Since then, she’s appeared on more adult shows, including Gossip Girl and Law & Order: SVU.
10. Shia LaBeouf
Shia LaBeouf won a Daytime Emmy Award for his role as Louis Stevens on Even Stevens, which ran from 2000 to 2003. LaBeouf has said he grew up on the show. He also starred in the 2003 Disney film Holes, based on the novel by Louis Sachar.
LaBeouf grew up fast, picking films that catapulted him into the unlikely role of action hero. He beefed up and dropped the boyish charm for the Transformers series, but things have only gotten edgier (read: more nudity) since then. LaBeouf bared it all in a Sigur Rós music video, and he’s currently filming Nymphomaniac, a movie that may or may not include unsimulated sex.
11. Lindsay Lohan
After several years of child modeling and soap opera work, Lindsay Lohan earned the coveted starring role in Disney’s 1998 remake of The Parent Trap. She then did the Disney Channel Original Movies Life-Size and Get a Clue before starring in another Disney remake, 2003’s Freaky Friday.
Oh, gosh, where to begin. Arrests. So many arrests. And court appearances, DUIs, and other legal troubles. All that aside, Lindsay has taken on increasingly raunchy and explicit roles, including a stripper in the thriller I Know Who Killed Me, a topless bad girl in Machete, and Tara in the highly anticipated The Canyons. She also posed nude as Marilyn Monroe, which is pretty tame compared to everything else. Needless to say, it’s been a very long time since anyone considered Lindsay Lohan “wholesome.”