6. REESE WITHERSPOON AS TRACY FLICK IN ELECTION (1999)

At this point in her career, Reese Witherspoon is known for tame romantic comedies and awards season projects. But that wasn’t always the deal. Back in 1999, the future Academy Award winner broke into Hollywood producers’ eyesight in Alexander Payne’s edgy high school comedy Election. It remains the darkest role of her career.

To Witherspoon’s credit, she played a rather despicable character for laughs and inarguably succeeded. As the mental and vindictive Tracy Flick, she’s a class presidential nominee with a scandalous backstory: Tracy screwed one of her professors, which led to teach losing both his job and wife. So, yeah—she’s well qualified to enter the world of MSNBC coverage. You’re nobody in politics until you’re outed as a one-time sexual deviant.