Factual error: Otisville Prison was not in the direction Monty's father was driving. He said he would take the Henry Hudson Parkway north and later continue on the Taconic Parkway. The Taconic runs due north toward Massachusetts on the east side of the Hudson River. Otisville is 30 miles west of the Hudson.
Continuity mistake: In the beginning of the movie where Monty is looking at his old school photo, look closely at his beard. In the next scene when he's in the classroom talking to 'his old friend' his beard has a completely different shape.
Continuity mistake: In the scene where Monty is about to leave for jail, Naturelle goes to get ice for him. She pulls open a drawer and grabs a quart size Ziplock bag and starts to fill it with ice. They cut to Monty and when they cut back to Naturelle she's filling a gallon sized Ziplock bag. (01:51:00)
Audio problem: When the police officer sits down on Monty's couch he asks if he could sit down and Monty says "Be my guest," but his lips move about a second late. (00:28:00)
Continuity mistake: In the scene where Jacob and Frank are in a restaurant together eating Chinese food, seated in a booth across the table from one another, Jacob has a tan jacket that is placed next to him, on the seat, to his right. Throughout the scene, as the shots cut back and forth between Frank and Jacob, the jacket next to Jacob repeatedly disappears and reappears. (00:53:20)
Continuity mistake: In the scene where Monty and his father have a whiskey together in Mando's Bar, the shots they drink are more full than what the bartender pours for them. (02:02:55)