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In between caring for her mother, a young woman works part time at a prison. The rookie guard gets a chance to prove her mettle when she's tasked with accompanying a hell-raising inmate on an emergency furlough to visit her dying mother. But things soon spiral out of control, sending the pair on a hilarious, surprising, and ultimately touching road trip.

A successful, ego-maniacal architect who has spent a lifetime bullying his wife, employees and mistresses wants to make peace as his life approaches its final act.