Continuity mistake: In the first scene in Woody Harrelson's flat, Rosie Perez is in bed. Her top falls down, all but showing her breast; but in the next shot, she has covered herself up, but without moving her arms.
Continuity mistake: In the scene where Billy is hustling Sidney (best of five shots), when Sidney is taking his last shot, you are looking at the scene from above the basket. From this view, when Sidney misses his arms are seen to drop, but when the camera comes back to a close-up of him, his arms are still in the air.
Continuity mistake: At his girlfriend's house, Woody Harrelson takes off his hat and puts it in his pocket. This is separated into two shots and he is seen to put the hat in his pocket twice.
Continuity mistake: When Woody returns home after losing Gloria's savings, he drains his wineglass twice in a row without refilling it.
Factual error: Rosie is repeatedly shown buzzing in before Alex Trebek can even finish asking the question. In Jeopardy!, this isn't possible, you may only buzz in once the question is finished.
Continuity mistake: When Woody Harrelson and Wesley Snipes are arguing (with the guys that end up hustling Woody's character) Woody's character throws his hands up and you can clearly see him poke Wesley Snipes' character in the eye, which causes him to go back grabbing his face, then it cuts to him just standing there.
Continuity mistake: In the scene where Rosie Perez is on Jeopardy, just after double Jeopardy starts she buzzes in and her score is $8300. As she answers that question her score is $5100. When she buzzes back in o the next question her score is $5300. As she picks the next category it jumps to $9300.
Continuity mistake: In the scene when Raymond loses in a hustling match and threatens to cut people with a razor, Wesley Snipes tries to talk him out of it. In between scenes the money he has won switches from his right hand to his left hand, and back again.
Continuity mistake: After Gloria answers the first question on Jeopardy, which is worth $100, her total jumps to $1500.
Continuity mistake: At several points during the Jeopardy game, Gloria isn't holding the button to buzz in for questions.
Other mistake: When the Stucci brothers take the fake death photo of Woody at the end of the movie, The Stucci brother driving the van gets in and takes off before the other brother even had a chance to get around the back of the van.
Other mistake: In the scene at Wesley Snipes' house after he hustled Woody Harrelson, Kadeem Harrison has his hat on backwards, the shot cuts away and cuts back to him wearing his hat forward, and he then turns it backwards.
Factual error: In the Jeopardy scene, Gloria takes the category, "Foods that start with Q," but never says for $100.
Plot hole: Sidney's friends at the beginning act like if he made his fifth shot, he beats Billy. If Sidney had made the fifth shot, he would have merely tied Billy and they would've either gone to a playoff or just settled for a tie. Billy made all 5 shots and Sidney was shooting his fifth,so Billy couldn't lose, only tie.
Continuity mistake: In the scene towards the end of the film, Wesley Snipes asks Woody Harrelson to join him for one last hussle. During this scene the strings from Woody Harrelson's hoody move from shot to shot. First they are straight down, then one is over his shoulder, then straight down again, then finally over his shoulder again.
Continuity mistake: In the scene where Wesley snipes came over after he was hustled, Woody just came out of the shower. While they were talking, Woody goes from being wet to dry in several scenes. He never used a towel to dry himself off.
Continuity mistake: Right before Gloria leaves Billy, she tosses her red shirt onto the chair near the door. But as she's packing her suitcase, she removes the shirt from the bed.
Continuity mistake: Billy comes home after the match with Sidney. While having a conversation with Gloria the bottle of vodka is on a small table close to the bed. The next scene the same bottle is already positioned on the kitchen's table.
Other mistake: In the scene in the motel room, right before Woody Harrelson reveals that he lost the $2,500, Rosie Perez walks over to a standard light switch that is in the off position, lightly touches it, and the lights slowly fade out as if she'd slid down a dimmer switch.
Continuity mistake: When Sidney makes the bet with Raymond, Billy comes out on the court and begins to stretch. The next shot has Raymond going to his car to get his gun. In the background, you can see Billy come out onto the court and start doing the same stretching routine as before.
