Miley Cyrus
is another Disney teen queen turned titillating twentysomething. When her dad, "Achy Breaky Heart" singer Billy Ray Cyrus, returned to showbiz as an actor after years as a recluse in 2003, Cyrus, whose stage name is derived from her nickname Smiley, decided it was the career path for her as well. She guested on dad's show Doc and had a part in Tim Burton's Big Fish before landing the lead role in Disney Channel's split personality smash Hannah Montana in 2005. Billy Ray was cast as the dad (Big Surprise!) of her average teen by day, famous pop star by night character. By 2006, the musical series is cable's most-watched show for kids 6 to 14. It spawned two chart-topping albums, a big-screen blockbuster, a sold-out 54-date concert tour (on which her boyfriend Nick Jonas' brotherly band is the opening act), a billion-dollar merch line and a seven-figure book deal. People's richest kid in 2008 still had to do chores, attend church and live on an allowance. The show's success helped Cyrus transition to making non-Montana music, 2008's Breakout, and films like Bolt and 2010's The Last Song. On that tearjerker's set, she met current fiancé Liam Hemsworth, who proposed in 2012. Since Hannah finished in 2011, the current Two And A Half Men guest star has been stirring up controversy of the adult variety on the regular. Between dramatic dye jobs and haircuts, a leaked video of her birthday bong hit (which she claimed was filled with the legal herb salvia), pregnancy and eating disorder rumors, side- and under-boob photos, her tattoo addiction and her scandalous Tweets, it seems boring days are few and far between in her world.