Most Infamous Moment: In 1993, Doherty's ex-fiance, Dean Factor, filed a restraining order against her after Doherty allegedly pulled a gun on him and threatened to hire a few guys to beat him and sodomize him. 

In the 90s, Shannen Doherty was the ultimate Tinsel Town bad girl. She was booted from 90210 after being deemed impossible to work with by producer Aaron Spelling, she bared all for Playboy magazine and even married notorious Hollywood bad boy Rick Solomon, who you may remember as the night-vision casanova from the infamous Paris Hilton sex tape.