Affleck and Mara play Bob and Ruth, two lovers who commit an armed robbery and get caught by the police. Bob takes the fall and goes to prison, forcing Ruth to raise their child by herself under the watch of their mutual father figure Skerrit (Carradine). Meanwhile, Patrick (Foster), a friendly police officer who helped arrest Bob, tries to ingratiate himself into Ruth's life. When Ruth learns that Bob has escaped from prison in an attempt to rejoin his family, Ruth faces a difficult choice on what to do.
The film was Lowery's directorial debut. While not a financial success, it was lauded by critics and put Lowery's name on the map.
- Bittersweet Ending: Bob dies in Ruth's arms shortly after reuniting with her. He wants to see his daughter, but she's carried away by Patrick to spare her from witnessing her father's death. The couple's father figure Skerrit has also recently died. However, Ruth and Sylvia survive the film unscathed and with their futures open.
- Blatant Lies: Bob tells a tall tale of his prison escape in which he nonchalantly walks out of prison because he has "better things to do." Sweetie has already heard the real story of his escape.
- Bounty Hunter: Three arrive in Meridian to try to catch Bob.
- Briefcase Full of Money: Bob stuck the haul from his robbery in a suitcase and buried it outside their hideout. He and Sweetie dig it up after Bob escapes prison.
- Dogged Nice Guy: Patrick is interested in Ruth and finds excuses to visit her. While he is always extremely polite and respectful, he's also choosing a rather difficult time to start wooing Ruth, with Bob being loose.
- Dramatic Irony: Patrick pursues Ruth without knowing that she was the one who shot him, not Bob.
- Great Escape: Off-screen. Bob makes up a tall tale about his escape, but Sweetie says he heard he just jumped off a work truck.
- Happy Flashback: The film ends on one in which Bob tells his grand plans for the future to his unborn daughter.
- Outlaw Couple: Ruth and Bob are explicitly based on Bonnie and Clyde.
- Period Piece: The film seems to take place around the 1970s, based on the cars, but Bob wears a somewhat anachronistic fedora that is probably a reference to the film's Bonnie and Clyde inspiration.
- Silence Is Golden: The film features many quiet and understated sequences.
- Tracking Shot: The film features a motif of the camera following behind a character as they march forward, filmed in SteadiCam.