After Paramount Pictures turned down the pop track for its film Fire with Fire (1986), Sean Penn took the track "Live to Tell", performed by his then wife Madonna, and placed it in this movie. The track went to #1 on the Billboard charts in June 1986.
When Christopher Walken works with guns in film, he checks them himself before each scene for safety reasons and his own personal ease. During the scene when Sean Penn sticks a gun in Walken's face, Walken checked the gun before the scene started. Before the director had the chance to say "Action", Penn ran off camera and shouted, "Give me the other gun!" He immediately returned to Walken and started the scene. This is the cut that made it into the movie, and Walken was really terrified.
When Brad Sr is being walked into the courthouse after being arrested, the building behind him is the Williamson County Bank located in Franklin, Tennessee not in Pennsylvania where the events took place.
In the first heist after Brad quits his dad, they are stealing tractors from the Franklin Implement Inc which is where the film was made in Tennessee rather than Pennsylvania where it took place.