ARGANDA DEL REY, SPAIN - JUNE 06:  Singer Miley Cyrus performs at the ''Rock in Rio Madrid'' music festival on June 6, 2010 i
Carlos Alvarez

Flip through any tabloid, and you'll likely spot paparazzi shots of the still-underage Miley Cyrus in bra-revealing clothing. This is no big deal when compared with the handful of micro-scandals she's already racked up: There's the icky photo shoot with her dad, the come-hither pictures that allegedly leaked from her cell phone, and more recently a video for her single "Who Owns My Heart" that's gotten parents' knickers into a wad because she's mostly in her underwear. (The latter is from her subtly titled "adult" album Can't Be Tamed.) Of course, this only earns her more attention.

When exactly did the "Party in the U.S.A." girl become so disdainful of her tween appeal? Maybe it's because she's turning 18 next month — a milestone that come spring will be greeted by the series finale of Hannah Montana. But with her short-attention-spanned following deprived of a weekly TV series, what has Cyrus really got to lose? Though it's treated like breaking news, the singer is simply following in the footsteps of a slew of other teen-dream pop stars with carefully calibrated careers who've smartly hastened a move into adulthood.

Britney Spears practically pioneered the innocent-school-girl gone bad business model, the switch precipitated by the release of her sweaty, exotic "I'm a Slave 4 U" video and provocative live performances. Her boyfriend at the time, Justin Timberlake, followed suit, ditching 'NSYNC, smoking weed, hitting the gym, and posing topless for the cover of Rolling Stone. Suddenly, his fans' moms took notice. And with "Dirrty," Spears' steel-lunged rival Christina Aguilera dove into adulthood feet first by 86ing her white-as-the-driven-snow image for something more Our Lady of the Pole. Their overtures worked.

Cyrus' contemporaries also seem to be on that same trajectory. Joe Jonas, age 21, is pulling a Timberlake by releasing a solo album early next year that someone in his camp has ominously said is "a more dangerous sound" than the output from his day job with the Jonas Brothers (also a Disney creation). He's reportedly ditched that purity ring; expect his shirt to come off next.

Gossip Girl's Taylor Momsen has worked diligently to cultivate her Courtney Love meets Cherie Currie image. The 17-year-old crawls across a dinner table on all fours in the "Miss Nothing" video (for her band, The Pretty Reckless), frequently dons lingerie as stagewear, and uses gobs of kohl to make menacing her cute-as-a-button face. Even 16-year-old heartthrob/hair icon Justin Bieber is showing early signs of demographic dyspepsia: Earlier this month, he was photographed publicly making out with fellow singer Jasmine Villegas, which caused a massive Twitter backlash among his admirers.

Like Spears and Timberlake and Aguilera, these restless pop stars are surrounded by a wall of publicists, managers, agents, and producers.Though, judging from past crossovers, it's the latter that are going to make or break the stars' transitions. Spears outsourced edgier contributions to The Neptunes to offset those of her go-to Swedish one-man bubblegum factory, Max Martin. Timberlake, who co-wrote his songs, also paired with The Neptunes and found a fertile collaborator in Timbaland. And Aguilera made-over her career after recruiting Scott Storch and Linda Perry to lend her bite.

Despite all her brazen rebellion, Cyrus is still working with her Disney-anointed producers (her record label is Hollywood Records, owned by the company). But with Hannah Montana close to an end, perhaps it's time for Cyrus to take a real risk and detour away from the Disney machine, just as her devotees increasingly have. Because the lesson learned from pop stars past isn't that sex sells — it's that if you want a career that endures, you gotta grow up with your fans.