Set in 1969, Alan Parker (Jackson) is a young artist, studying at the University of Maine. He becomes obsessed with death, and believing he is losing his girlfriend, Jessica (Christensen), he tries to commit suicide on his birthday. His friends manage to stop him, and he eventually recovers and decides to go with them to a John Lennon concert. Before he leaves, however, he receives news that his mother, Jean (Hershey), has had a stroke and is near death. Alan decides to hitchhike, in an attempt to reach the hospital before his only relative dies.
After getting rides from increasingly unusual people, he is picked up by George Staub (Arquette). Staub turns out to be dead, and is a form of the Grim Reaper, who collects souls. Staub is omniscient in his knowledge of Alan's life, and Alan has to make a decision which will determine whether he or his mother dies. Later on he escapes from George and ends up riding The Bullet, a roller coaster he was scared of as a kid. George captures him once again and he choose for his mom to die. George throws him from the car. He wakes up to a grave, George's grave. He hitches a ride to see his mom. When he gets there he keeps thinking negative thoughts, feeling badly about his choice. The secretary tells him everything. He looks in his pocket and finds what had George had given him and sees George in the elevator. He goes hurriedly up to his mom's room but the nurse says she is sleepy. She goes home a couple days later. He starts skipping years. His mom quits smoking and then a little bit later picks up smoking again. In 1972 his mom was laughing and then stops, he goes and checks on her, to discover she has died. The movie skips to his marriage to the girlfriend from the beginning. He then says the marriage did not last long. He turns the projector off. It shows a elderly Alan. He goes outside and reveals he never got the job at painting but still likes to do it. It then shows him painting a picture of his mom. The movie then goes to credits.