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Fight Club is a classic but it hasn't been around as long as a Clockwork Orange. Fight Club had a better ending, better dialogue, better actors, and it was overall, not by much, more entertaining IMHO. Fight Club was very entertaining and it did that without having to sacrifice the messages or themes they were trying to get acrossed. A Clockwork Orange does explore themes much deeper than Fight Club but in doing that kind of sacrifices some of its entertainment value. Another reason why is because I relate a little bit more with Fight Club, being stuck in that whole generation of men raised by women group. They are both great movies, but I went with Fight Club.
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