Two thoughts:
1) Older women (men too, sometimes) are usually better lovers due to experience level. Throw in the fact that Jennifer Anniston is beautiful, smart and funny, and you have an unbeatable combination.
2) I personally - yes, even tho I am female, for purposes of this discussion, i am thinking like a guy - I personally would do Jenifer Anniston over Jessica Simpson. While pretty, JS is dumb as a bag of hammers, and tho I realize that to most of you, IQ points have no bearing on poon, you do have to talk to them at some point. Better if you don't have to use pictures and words of three letters or less.