I don't really watch gambling movies buy recently, I have watched 'The Gambler'. Since it's the only gambling-related movie I've watched so far, I don't know if I'd already consider that as my favorite gambling movie.
But anyways, it is an interesting movie. It's about an English professor, named Jim Bennett, who happens to be a high-stakes gambler. Based from what I saw, he does not try to win whem he gambles. It seems like his primary goal is to lose because he always doubles up on every single hand which is a sure way of losing everything in just a snap of a finger. Bennett bets it all and then offers his life as collateral. He tried to borrow money from his wealthy mother. Unfortunately, she refused which drove Bennett to borrow from a loan-shark just to pay-off his debt of more than a quarter of a million dollars to the owner of an illegal gambling den.
At the end of the movie, Bennett said that, "I am not a gambler." Maybe because of the fact that true gamblers would like to win and have an aptitude of playing cards. But he is the opposite. He was seeking the loss.