7. One Flew Over The Cuckoo's Nest
This movie shoves your friend's face over the edge of a desolate precipice into a very dark void. "Why do anything about anything?" your friend grimaced as you watched Chief Bromden hang onto Mac one last time. "If we do, they'll put us on medication or outright lobotomize us." "Who?" "Those in power. It always happens, every single time we try to do something. And you can't get others to help you, because they accept what's around them, and if they don't, they'll just get arrested or killed. Or lobotomized. We're trapped, man. Trapped. We have to keep our heads down to not piss them off. Our system just eats its inhabitants from the inside out. There's no room for dissent." At that point, you thought it might help to say something. "Don't you think this movie is more than that?" "No. There's just nothing here for any of us but despair." Until you asked him what movie he wanted to see in the theater that weekend! But if there's anything worse than being a Tim Curry cloud, in middle school, killed, or lobotomized, it's the prospect that society can't change even if none of those things were around. Which is what your friend thinks whenever he watches the next movie on the list, and thus far your attempts to steer him clear of that prospect have been largely unsuccessful.