One of the main reasons I'd really love to be wealthy (aside from obvious reasons) is that I could do hilarious/expensive things. I've always envied celebrities like Bam Margera for this reason.
But one thing that I've been thinking about for a bit. Have you seen those Chevy HHRs without rear windows? The panel side or whatever.
If I had the money to throw around, I think it'd be hilarious to buy one, lift it, add huge wheels, and paint it up like a mini Gravedigger.