The Gambler Returns: The Luck of the Draw (1991)

The Gambler Brady Hawkes is back and he's about to lose his primary means of livelihood, when a law banning gambling is about to be passed. But in honor of that there's going to be one last great poker game and all what one needs to join is one hundred thousand dollars. A madame named Burgundy Jones along with four other madames is willing to put up the money for Brady but first he has to compete against four other gamblers in the end it comes down to Brady and a man named Cantrell. Brady barely beats him. So he, and Burgundy, and an old friend of his, Ethan Cassidy sets for the game which is in San Francisco. But Cantrell's a sore loser and is following them hoping to get the money so that he can join the game. Also following them is a band of outlaws who were planning to steal the money but Brady left with it before they got there. And along the way they encounter and/or are aided by some famous individuals like Wyatt Earp, The Rifleman, Cheyenne Bodie, Diamond Jim Brady, Bat Masterson, Judge Roy Bean, and President Teddy Roosevelt. Brady is also feeling that he might not have what he has to win; it seems that some time ago in Europe he lost a big game to an Englishman, and by strange coincidence he is also at the game.