...if we're talking casino betting,
Sean Connery's your man (surprisingly good at baccarat and blackjack, knowing how to win enough without pissing off the casinos apparently).
Ben Affleck's supposed to be a much better gambler than his compadre, Matt Damon (who as some of might know as part of getting off the buzz of filming
Rounders, tried out for Binion's World Series of Poker a few years ago and promptly lost all his deposit in the first round. Oy!
).