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I think it was someone on here who pointed out that he essentially plays the same character in every series. In Lost, Betty and the O.C. he's a powerful boss of a company and father of an important character. He also dies a lot.
Hmm, last week I would've voted Jim no doubt, but after Widmore's evil "you're not good enough to drink my whisky, so you can't eat my daughter" rant(as Tomtrak described it), I'll have to go with that.