This is an awesome question… Love it!
My favorite gambling-esque movies are:
Rounders, with Matt Damon & Mike McDermott (LOVE this one… if you haven’t seen it… it’s a MUST!!!)
Casino, with Robert De Niro, Joe Pesci & Sharon Stone
Oceans 11 & 12, Brad Pitt, George Clooney, Matt Damon… and several others