5. Drew Carey
Apparently when you are one of the richest stand-up comedians in the world you can afford to make your waiter happy by leaving big tips.
From being a comedian and producer his net worth is pretty solid and so are his tipping habits.
Once he dined at Arnie Morton steakhouse in LA and put together a tab for about $250.
He was a gentleman and left a $400 tip, almost he doubled the bill.
Good guy, Mister Drew Carey! We like you!