After losing his initial stack to John Malkovich, Matt Damon has to play him again in order to pay off the debt Ed Norton owed against his name (who subsequently bailed). After winning enough to pay off the debt, Damon continues playing and beats Malkovich ending up with exactly the same pot he had at the start of the movie.
Continuity mistake: In the scene when Worm and Mike go to see Gramma about Worm's debt, Gramma says, "What's the matter, Lester? You looking for a little charity?" Worm curses at Gramma and takes the toothpick out of his mouth and throws it on the floor. Gramma grabs Worm immediately and the toothpick is back in Worm's mouth.
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