Continuity mistake: When Ray and Claude are going to bed in the retirement home, Ray tells Claude that he's going to put his wet sheets on him when he's sleeping. If you look closely Claude starts laughing really hard, but he's not supposed to.
Continuity mistake: When Claude and Ray are first put in jail, Sheriff Warren Pike's cut is straight up and down. At the end of the movie the scar is at an angle.
Factual error: As Ray is fighting the big inmate over the cornbread, Ray falls over, revealing a yellow patch on the bottom of his boot. That patch is the trademark of a Vibram sole. Vibram started using the yellow patch in 1965. The scene takes place in the 1930s.
Other mistake: When the prisoners take a break from digging the ditch, Jangle Leg sits down to talk to Claude. When Claude looks at Ray in confusion while Jangle Leg is still talking to him, you can see Jangle Leg sitting down below Ray.
Revealing mistake: In the scene where Claude and Ray are arguing about the loss of the appeal and Ray calls Claude "soft", watch as Claude swings the first punch of the fight, his fist misses Ray's face. This is even more obvious in slow motion.
Continuity mistake: When Ray and Claude first enter the diner, there is nothing on the door. Later in the scene, the woman asks them if they can read so well how come they missed the sign on the door that says "No Coloreds Allowed"? The sign wasn't there when they first came in and it's not there when they leave.
Continuity mistake: When Claude & Ray first set off in the car, Ray's shirt is un-buttoned when the camera is pointing from Claude to Ray, then it's buttoned when the camera switches, this continues to happen throughout the scene.
Factual error: In the scene where the jail warden's grand daughter has her baby and he is shocked to see that he is African-American, he goes to the jail to find out who the father is. She had just had her baby but when he holds the baby up to each inmate, that baby is at least 6-9 months old.
Factual error: When Claude is standing outside the car while waiting on the current warden to pick up the new warden, he's looking at the different styles that have come to pass while he was in jail. It it supposedly the 70s but when Claude looks at the guy with the stereo he hears Maxwell's "Fortunate" on the stereo. This song came out in 1999, not in the 70s.
Continuity mistake: In the scene where Claude and Ray enter the "white only" diner, they enter leaving the door open. When the waitress asks them if they saw the sign, they look back and the door is closed. When they get ready to leave, the door is open again.
Continuity mistake: When Ray and Claude first arrive at prison, they are walking by the inmates. They walk by Biscuit (who's wearing a red bandanna), then they walk by Willie, he's narrating the story, then it cuts to them walking by Biscuit again.
Plot hole: Claude was asked to fill in as a driver for the commodore, however, this is strange considering he obviously doesn't have a driver's license and hasn't driven in over 40 years.
Continuity mistake: When Claude and Ray have just loaded the truck with the booze, Ray hears music and is trying to convince Claude to go to the club. Ray is holding up money and from the back it is folded up but very messy and the roll is thick, From the front it is folded very neat and the roll is thin.
Continuity mistake: When Ray and Claude are talking in the car you see Claude looking straight forward while Ray is talking to him, but when it switches to Ray´s position then you see Claude looking straight at Ray and then he starts to talk.
Continuity mistake: After Ray and Claude stop talking, there was a little interlude where it shows time going by and a few inmates have died, one being Cookie. But after it shows Ray trying to escape with the plane and you can see Cookie with the rest of the inmates on the field looking up at Ray. (01:17:19)
Factual error: When Claude and Ray are in the car driving to get the booze, you can see they pass a home on each side with a more modern white truck at each home. These truck appear to be from the 70's or the early 80's when that scene is supposed to be in 1932. (00:12:40)