When I'm back in Chicago and working I am borderline overboard on tips, there's been nights where I've tipped the servicepeople more than I've spent at the establishment.
My philosophy is this: When I'm not saving up for my money to take down to college I make enough money at my job here where I can drop a good $250 in a night and get away with it. I usually have no intention of running up a bill that high so I tip everyone in the place like a madman the second I walk in. I get impeccable service, I wait a minute max for any drink. The people who work at these places talk to each other, and if the waiter gets $20 before he even takes your order you better believe he's gonna tell all his pals. It gets expensive, sure... but I really dont spend my money on anything else (no car and I despise retail consumerism) so I might as well have a great time spending it.
This changes when I go back to school and am poor as hell, I still tip but never over 20%. Service is never that great down here anyways, I dont expect it to be.
note- chicks totally dig it when you spend money like it's nothing (I know where that comes from), and it's a lot more fun for you and the people you're with when the entire staff tries to make all of you feel like royalty.