Great thread. I know lots of ideas are going to occur to me about this one.
For starters, I like explorers - so how about Ranulph Fiennes ?
http://en.wikipedia.org/wiki/Ranulph_Fiennes
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Rolex Sea Dweller 116600, GMT Master II 16710 (Pepsi) and 116710 BLNR, Daytona 116500LN, Submariner 14060M.
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