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Midnight Cowboy is more fun (and weird) and Dustin Hoffman played his part perfectly. I don't really get The Graduate, except I do and I hate it, along with Dustin Hoffman being in it.
Both of these are hailed as classics but I found both to be overrated.
What watching iconic Dustin Hoffman movies has taught me is that I dislike iconic Dustin Hoffman movies. But I hated THE GRADUATE, so MIDNIGHT COWBOY wins by default.