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I second Jake and Elwood Blues.I would also like to nominate Carl Sagan, sure he may have been a scientist, but the man also liked to just chill out smoke some pot and relax.
I second the Clint Eastwood and Dalai Lama nominations. I always thought both of them were dudes.
I nominate Zonker Harris from the comic strip "Doonesbury". Zonker is one of the most Dude characters I can think of and he has been a Dude for about 40 years. His many titles and accomplishments include: Greatest Living Slacker, SPF 0 Solar Collector, Lifetime member of the Malibu Cannabis Buyers Club, Hippie, Ol' Surfer Dude, Prince of Inner Space, Excellence in Tanning at the Gerald R. Ford Summer Biathlon, and the all important reputation as a Freak. I think Zonker would be an excellent addition to the "Great Dudes in History" Hall of Fame.
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