66. Jenna Jameson
Age (circa 2009): 35
Occupation: Adult Video Star
Blonde Barbie doll Jenna was the biggest paid sex worker in the biz and even managed to cross over into mainstream, doing film work and creating her own comic. All this and she never did anal or interracial, which is of course to say that she's not very big at our crib.
Rather than list the numerous videos we've come to adore her in, we'll be classy and say her top moment in the Aughts came in 2000 when she became a business, and launched ClubJenna.com