Ride with the Devil follows four people who are fighting for truth and justice amidst the turmoil of the American Civil War. Director Ang Lee takes us to a no man's land on the Missouri/Kansas border where a staunch loyalist, an immigrant's son, a freed slave, and a young widow form an unlikely friendship as they learn how to survive in an uncertain time. In a place without rules and redefine the meaning of bravery and honor.

Steve Brooks, a sexist womanizer, is killed by a group of his angry former lovers. In heaven, he makes a bargain with God for redemption and agrees to return to Earth. Once there, he must have a sincere relationship with a female and make her fall in love with him. If not, Steve's soul will become the property of the devil. But the devil hedges his bet, and Steve is reincarnated as a woman named Amanda Brooks.