5. Ethan Hawke as Troy Dyer, Reality Bites (1994)
Though he appeared in Reality Bites long before anyone even knew what a hipster was, there's no doubt about it: Troy Dyer (Ethan Hawke) is a total hipster. Let's look at the clues: He’s a coffeehouse guitarist in a band that covers Violent Femmes songs, which is named Hey, That's My Bike! He talks darkly and deeply about Quarter Pounders with Cheese. He has no real job to speak of, and seems to flit from one minimum wage job to the next. Still, somehow, he's not homeless. It's all for the sake of the art, man.
He’s also an asshole, especially to his best friend Lelaina (Winona Ryder)'s new boyfriend, simply because he's a suit who works in television. Putting aside how it's grade-A asshole behavior to judge a person based simply because they're not all deep about cheeseburgers like you are, Troy seems to show no regard for how Lelaina might feel about him being a dick to the guy she's dating. Of course, his actions are only masking the deeper, romantic feelings he feels for Lelaina, but insecurity is no excuse for that.