The Executioner’s Song begins with Gary’s release from prison, with the idea of prison and imprisonment becoming a key motif in the text that reflects Individual Will Versus Societal Control. Gary has spent so many years behind bars that he is determined to embrace his freedom. He does not want to return to prison, so prison becomes a symbolic reminder of what he stands to lose. While Brenda accepts the sincerity of Gary’s stated desire not to return to prison, she cannot separate him from the prison itself. The optimism that Gary showed when he left prison metastasizes into something darker while retaining its symbolic significance. Gary is afraid of returning to prison, but also afraid that he is too thoroughly shaped by prison to ever truly be free.

The book treats prisons as more than just physical buildings. Many of the characters are trapped inside metaphorical prisons, which are just as inescapable and as totalizing as the structures that hold Gary. Vern is imprisoned by his material conditions, as he struggles to support his family financially and struggles to save up for an operation to fix his ailing body. Nicole is trapped in a series of failed relationships. Even as she tells herself to abstain from men or romance, she feels unable to abandon these relationships entirely. She suffers physical and sexual abuse at the hands of a series of men and feels unable to be alone, even as she knows that such relationships are unlikely to end well. She feels trapped in a prison of trauma, a prison that a relationship with Gary initially seems to offer her a release from. 

After committing the murders, Gary returns to prison. He spends the rest of his life in prison, a symbolic return to the same institution that has shaped him so completely. Gary hates the prison because it represents his loss of freedom, but he feels at home behind bars. For Gary, the tragic truth is that he is better suited to prison than society, which is one of his reasons he gladly accepts his own annihilation.