Jack DeWitt is Clueless is a classic coming of age story set in the backdrop of the 1960s. Jack experiences the beginning of the decade as a junior high student growing up in a Midwestern factory town. He loves books. He hates sports. He's not sure girls like him. And then he has this pimple situation. Through Jack, we experience the main events of the early 1960s: the Civil Rights Movement, the Vietnam war and the protests it engendered, the assassination of JFK, the influence of Martin Luther King Jr., and the songs of the Beatles and Motown.

Jack also experiences monumental events closer to home. The house belonging to the only black family living in Jack's neighborhood burns down in the middle of the night. The fire was obviously caused by arson, but the police hardly bother to investigate it. Exactly one year later, the white man suspected of setting the fire is found murdered in his garage, his head smashed in with a hammer.