The film opens with Luke cutting the heads off parking meters. The cops bring him in. We then see a group of prisoners doing work clearing a road of grass that’s overgrowing. Luke then arrives at the prison where he’s been sentenced to two years. He begins to get accustomed to the daily hardship of the work as he integrates with the other prisoners, but in the process finds an adversary in Dragline who boxes him in the yard after days of contention between the two. Luke gets the tar beat out of him, but refuses to stay down when he gets hit. It’s hard to watch but he eventually wins the respect of Dragline who walks away from the fight.
The same night Luke plays poker and keeps raising the pot until it’s so rich everyone folds. He wins the hand with nothing and Dragline tells him it’s the same as he had in the fight...nothing. “Sometimes nothing is a real cool hand.” With that Dragline give Luke his nickname, Cool Hand Luke. The next day Luke gets a visit from his mother, brother and nephew. He says goodbye to his mother knowing that she will be dead before he is released.
The next day the men are given the job to roll an entire road with tar. Luke energizes the men to make a game out of tarring the road, to do it faster than anyone expected they would. By doing so the spirits of the men are lifted when they have two hours of daylight remaining in the day when they don’t have to do anything. Luke then tells the guys he can eat 50 eggs in an hour to which everyone gets in on the bet. Luke does it and it thrills the men. Later, Luke gets a letter that his mother has died, and instead of being given the opportunity to mourn he is thrown in the hole for the night because they believe he will run.
Once Luke is let out he cuts through the floor in order to escape. He’s able to run for a day but is eventually caught a mile and a half away. A few days later Luke escapes again. This time he gets away and some time later sends a picture to Dragline of him with two women in a bar. Luke is caught, beaten and brought back to the prison where he tells the other prisoners that the picture is a phony. The bosses break Luke’s spirit turning him into an yes man and all of the prisoners are disappointed by his loss of will that he had so strongly before. But when Luke is on the chain gang he deceives everyone as being an imbecile that does whatever the boss does, but when the time is right he steals a truck and runs off again and this time with Dragline. Luke makes his way into a church where he is surrounded by the prison guards and shot in the neck. Dragline carries Luke out to them and when the police say to take him to the hospital the Captain refuses and drives him an hour away to the prison hospital so that he will bleed out and die on the way. The film ends with Dragline telling the men what happened to Luke and how he drove off with a smile on his face.