8. Rory Cochrane as Lucas, Empire Records (1995)
There’s no question that Lucas is a hipster. He, like many of his kind, works at a record store and judges people to hell and back if they don’t share his taste in music, all very typical and irritating in their own way, of course.
However, that's not what makes him particularly annoying, not to mention an awful person. What makes him an annoying and awful person is the fact that he ends up fucking up a major deal to sell the record store he works in to a chain of music stores, Music Town, all because he doesn't want to work for "the man," which in this case would be a large corporation that could potentially offer him and his co-workers more financial benefits than any independent business could. All for his principles.
The best part, though is how he fucks up the deal. When he discovers that the store is in danger of being sold and that his manager, Joe (Anthony LaPaglia), is interested in buying the store from the owner rather than having it sold to Music Town, Lucas decides it'd be a great idea to take the money that Joe's been saving (total: $9,000) and gamble it in an effort to double it. Unsurprisingly, he loses it all.
If you're going to screw up a major deal that could benefit a whole group of employees just because you don't want to be an employee in a large company, don't do it with the money some poor guy's been saving to do the same thing you're doing. That's just called being an awful person. Even the Occupy Wall Street guys would hate this dude.