I nominate two of the Dudeist dudes ever
Groucho Marx - for always saying the right thing
Winston Churchill - for sitting on the roof of Downing street with a bottle of Brandy and a stogie and watching the Blitz - he abides
I agree, both dudes were pretty Dude. The latter especially, although the former's almost zen-like quips have made their mark in history. Churchill was one of the most laid back dudes, but he still ruled with a strong hand. However, seeing as he is so revered, perhaps he wasn't the best of Taoists.. after all, when the greatest ruler has gained great success, it is the people who think they have achieved.