Sean Penn's bad boy image stemmed in part from his romantic involvement with a string of actresses. While working on Dead Man Walking (based on a book by Sister Helen Prejean, whose character was played by Susan Sarandon), Penn approached Prejean one day with a message from his mother. "Helen," he said, "my momma said to tell you that she's glad I'm in a movie with a nun."

[Though Penn had retired from acting in order to direct, the screenplay quickly changed his mind: "When you read a script and your tears have fallen on a page," he explained, "then you know it's something you have to do." His character was a composite of two death row prisoners with whom Prejean had corresponded and seen executed.]

[Eddie Vedder (Pearl Jam's lead singer and a friend of Tim Robbins) was asked to contribute a song for the film. His reply? "Man, I'm for the death penalty, that's why I stopped belonging to Amnesty International." Vedder, persuaded to see the film, promptly changed his mind and contributed two songs to the soundtrack.]