Billy Crenshaw has a terrible hangover. A barfly and struggling writer, he's woken up alone in a strange bed after blacking out during a bender. But his hangover's the least of his worries; for on top of suspecting he's cheated on his girlfriend, he vaguely recalls that something awful has befallen his best friend Danny.

That's when he meets Bobby, the only other person in the Ann Arbor apartment that Billy has woken up in. At age six Bobby's convinced he's a cowboy. Moreover, he's convinced his daddy is too, though in reality the latter is a deadbeat dad who abandoned the kid and his mother. Yet Bobby won't relinquish his fantasy: to Billy's horror, Bobby plans to train-hop at the nearby train station and skip town in search of his father.

The two of them then reach a compromise. If he behaves, Bobby can go with Billy as he scours Ann Arbor for Danny, a gifted musician who's headed for stardom if he can only conquer his demons. And in return for not train-hopping? Ending "happily ever after", Bobby's price is a fairy tale told by Billy that stars the kid and his daddy as cowboys.

As they search for Danny, though, they slowly discover that life itself is often far from a fairy tale...