Convicted murderer Clyde Thompson receives the death penalty for shooting two men in Texas in 1928. When the governor spares his life, Thompson gains a reputation as the meanest man in the state while working hard labor in prison.

Former high school friends run into each other years later and drunkenly decide to make good on their promise to marry each other if they're both still single by 30 - only to discover too late all the things they liked about each other when they were younger have changed.