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Jenny McCarthy has moved into batshit crazy territory the past few years, but she has aged much better and can still pull off the secretary/office look.
I had to vote for Pamela Anderson in this one as I just think back in the day she was better looking. She has that typical playboy look, and while that might not be to everyone's taste, I do think that she's become synonymous with that certain 'look'.
Back in the day Pamela was much more beautiful then Jenny but Pamela has not aged very well. Jenny is the better looking one now but she is a bit on the crazy side.
