I just come up with a idea...
how about Monopoly with real money,
It must be fun, but main question is who will do the 'Bank'
you can play monopoly for bitcoin here Gambit.com the game is calles bitnopoly but its very similar to the original game
Yo i dont think you can win actual bitcoin though, you cant buy chips at the site with bitcoin. Then they just give prizes out on a points leaderboard. That is my understanding of it anyway. Its a shame.