I feel like your train ride has come and gone, but after agreeing with Life Aquatic and Life of Brian, I would suggest
Dystopian:
Brazil
A Boy and His Dog
Soylent Green
or
Humor:
The Big Lebowski
Bad Santa (Billy Bob Thornton's irreverent self)
Eagle Vs. Shark (with Jemaine, from Flight of the Conchords)
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