Alan Parker (Jackson) is a young, struggling artist studying at the University of Maine whose work is haunted by images of death. Believing he is losing his girlfriend, Jessica (Christensen), Alan's obsession with the dark side pushed him to try to take his own life on his birthday. Some friends thwart his desperate act, yet events go from bad to worse, as Alan soon discovers he has opened a door letting death literally enter his life.

Recovering from his self-inflicted wounds and about to embark on a road trip to a John Lennon concert with his buddies, Artie and Hector, Alan receives crushing news - his mother, Jean (Hershey), has suffered a major stroke and is lying at death's door in Lewiston Hospital, over 100 miles away. Rejecting his friends' offer to drive him, Alan decides to hitchhike, hoping he'll make it to the hospital before mom, his last remaining relative, passes.

But it is Halloween night - October 31st - and Alan is about to discover that he has started down a nightmare road which will take him on both an odyssey into black recesses of the human heart and a journey that will bring him face to face with Death Incarnate.

Trapped in a speeding car with the Grim Reaper, manifesting itself in the guise of a recently killed redneck George Staub (Arquette), Alan is forced into a terrible dilemma - the Reaper will not rest until it forces Alan to make a life or death choice.

Alan Parker is on a date with Destiny which will answer the question that has plagued him since childhood - is he ready to go Riding the Bullet?