The Dwarves, Bilbo and Gandalf have successfully escaped the Misty Mountains, and Bilbo has gained the One Ring. They all continue their journey to get their gold back from the Dragon, Smaug.

Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.