Al... Yankevic? Noooooo... Smart-funny- WIERD. Yeah. Totally NOT doinkable, sorry, no matter how rich he may be.
I'm thinking snobby "everything I own is Titanium and I shave my legs have like 0.6% body fat and refuse to own a car" (like my high school boyfriend! Ack! That's who I was after when I was 16! Yikes!)