60. Olive Pendergast, as seen in the film Easy A, portrayed by Emma Stone
Like just about everyone, I love the John Hughes movies from the 80s. He was able to capture adolescence in a way that very few have been able to since, perfectly encapsulating everything which is stressful, hilarious, exciting, and depressing which encompasses those years. While I have certainly loved "teenage" movies since then, there hasn't really been one that had that John Hughes feel until Easy A.
Easy A tells the story of Olive, an unpopular but witty girl who, in an attempt to get a weekend of peace, tells a lie to her best friend about losing her virginity. As gossip is wont to do, it quickly spreads, and suddenly Olive is a "slut." Rather than rage and sob against it, Olive decides to embrace the ridiculous slur, pinning a scarlet letter to her chest and faking having sex with guys to pump up their sexual credibility; as she does so, her popularity increases and Olive thinks it's hilarious and profitable, given that she receives cash and gift cards for her "services." However, she doesn't want Todd, the secret object of her affections (played by a particularly yummy Penn Badgely) to find out that she is running such a profitable business. And, like every girl who has a bad reputation in high school, Olive quickly learns how it can work against you; while on one of her "dates," the guy who has taken her out becomes too aggressive, using the logic, "I paid for you, so I get what I want." Olive realizes she needs to reclaim her sexuality rather than let everyone else determine it for her, and so she broadcasts a webcast which outlines the truth of what she has done.
What I love about Olive is, unlike so many depictions of teen girls, she doesn't freak out when people start to call her a slut. She knows it is both ridiculous and, in the grand scheme of things, not really a big deal. We can debate forever about pejoratives like slut, whore, and bitch, but the truth of the matter is, they only have as much weight as we put on them. When you're 16, being called a slut is the end of the world because it means no boys are going to want to date you, and that's the goal; Olive turns that trope on its head and makes it work (temporarily) for her. Now, of course, it goes wrong because Olive isn't old enough to understand what being "a slut" can mean to men: you have sex with anyone, so you should have sex with me, and, if you don't, you're a slut and a bitch. It's a hard lesson to learn, and it's, unfortunately, a lesson every girl ends up learning. Olive's attempts ultimately fail, but at least Olive tries to fight against the twisted patriarchy which dictates high school (and regular) society.
And that's an empowering kind of kick-ass.