Drew Baylor, once a rising star at a leading athletic shoe company, has just been fired due to the overwhelming failure of his design for a sneaker and $972 million loss his company suffered because of the fiasco. As if that wasn't bad enough, things get even worse: Drew receives a phone call informing him that his father has passed away -- and now, he must get on a plan for Elizabethtown, Kentucky to retrieve his father's remains. On the plane ride, Drew meets Claire, a flight attendant and unstoppably positive woman who changes the course of his life. It is in Kentucky that Drew comes to learn the breadth of his father's life and his own family roots. Drew, with the help of Claire, submits to discovering the possibilities for his own destiny.