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In the early 1960s, Bobby Fontana (Lewis Smith), a young greaser-type rebel, challenges Joe Barnes (Mark Metcalf) to a game of chicken for making a pass at his girlfriend Emily (Jane Kaczmarek). Bobby wins the race easily when Joe dives out of his car, but Bobby is unable to get out of the car in time due to his bracelet getting caught on the gearshift. He dies as his car plummets over the cliff into a fiery wreck.

Bobby awakens to find himself aboard a speeding train, which stops at a station housing a huge escalator going up into a bright white light, which one of the attendants refers to as "Uptown". Bobby is denied entry, and Rafferty (Richard Mulligan) appears and explains that he is not yet considered ready and needs to carry out an "assignment" in order to earn his ticket Uptown. After many years in limbo, Bobby is finally given his assignment: he is to return to Earth and act as a guardian angel and friend for Lenny Barnes (Jason Gedrick), a promising high school student who is constantly picked on in school, particularly by school bullies Fred Gallo (Stephen Gregory) and Bill McIntyre (Beau Dremann). However, Bobby is instructed that he is only allowed to reveal himself to Lenny and nobody else.