One of my all-time favorite Dudes was Bill King, a long-time Bay Area radio sports broadcaster. The term "sports broadcaster" would disqualify a lot of would-be Dudes from nomination, but King was no ordinary broadcaster. He lived on a sailboat and was prone to showing up for work in a bathing suit and flip-flops and a Hawaiian shirt. He drove a beat-up old Trans Am with holes in the floorboards because he couldn't imagine anyone spending more than $200 on a car. Yet, he also loved the ballet and would unashamedly and unpretentiously work terms like "pirouette" into his commentary. He read Russian literature and grew the wicked facial hair of a Russian novelist, with the moustache waxed into swirls at the ends. He wore this look even in the 50s, when men were expected to dress like Eisenhower and have haircuts you could set your watch to (nod to Grandpa Simpson for that quote!).
I think King's Dudeist outlook could be summed up with this anecdote: he was asked why he had never moved to a larger market, say New York, where he could easily have gotten a gig with the New York Yankees and a much larger paycheck. King answered, in a wistful tone, "I don't think the Yankees and I would have gotten along."
Bill died in 2005, but for me he set the high water mark for Dudeism.
-V.