Deep in the heart of Iowa, at the CB&Q Regional Train Maintenance Yard, a downtrodden yard worker, Pa, shovels ballast, drinks muscatel, and sings a folk ballad to his beloved son, Martin, about the legendary Hellbound Train. Before the young boy’s eyes, Pa is killed by a passing train and young Martin is dumped at the local orphanage by his low-life “good-time” mother.

Time passes. Martin, a young teen, escapes the orphanage intent on living the life Pa always dreamed of, out riding the rails, free from responsibility. Falling in with the company of disreputable hobos, Martin eventually lands himself on a chain gang for stealing hubcaps.

Time passes. Adult Martin, newly freed from prison, contemplates changing his ways and joining the Salvation Army. At that moment, That Hellbound Train roars into view and Martin comes face-to-face with The Conductor, that mythological being of his father’s song.

The Conductor, eager to obtain Martin's immortal soul, offers a deal, one wish in exchange for “a ride on That Hellbound Train.” Thinking to outsmart The Conductor, Martin asks for the power to stop time and live forever in the happiest moment of his life - thereby avoiding ever having to board That Hellbound Train. The deal is struck, and The Conductor gives Martin his stopwatch imbued with the power to stop time - just once.

As Martin journeys through life, he is faced with the recurring question, “Is this that moment of perfect happiness?” Is happiness found in a bottle of muscatel and a dry cot in a flophouse? Is it in a series of flings and one-night stands? Is it the moment Martin meets his wife or the birth of his son? Will he find it in wealth, status, or the arms of a mistress?

Time passes. As an old man, Martin contemplates his life, both the beauty and the futility of his search. Unable to find this perfect moment, Martin dies and finds himself boarding that Hellbound Train, where he meets the “drunks and the drifters, gamblers and grifters” singing his father’s song; the song Martin loved as a child. When The Conductor demands the return of his watch, Martin has an epiphany…happiness is found in the journey, not the destination. To The Conductor’s horror, Martin stops time, ensuring That Hellbound Train and its merry band of sinners will forever journey, never reaching The Depot Down Yonder.