I know this is a different direction than what you're thinking right now, but it might give you an idea or two.
For my bachelor party, we held the Casino Olympic Championship. All the guys participated in blackjack, roullete, craps, that stupid game with the big wheel, and others (don't really remember 'cause I was drunk). We all kept a tally of how much we were up/down, then the biggest winner got lap dances paid for by all the other guys there. It was amazingly fun.
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