1962 is the worst of times, but also the best of times for Oliver Beene (Grant Rosenmeyer), an 11-year-old whose world is full of comedic chaos. Oliver's eccentric family is headed by his father, Jerry (Grant Shaud), a dentist whose idea of a fun and relaxing Sunday is drilling his kids' molars. Then there's Oliver's mother, Charlotte (Wendy Makkena), a homemaker who idolizes Jackie Kennedy and fantasizes about being her. The Beene household is rounded out by older brother Ted (Andrew Lawrence), a sports fanatic who lives by one simple rule: "If it ain't about sports, it ain't worth talking about." This is exactly why he and Oliver haven't spoken in four years.

Oliver's life is often made more bearable with friends Michael (Taylor Emerson), Joyce (Daveigh Chase, The Ring) and his crush Bonnie (Amanda Michalka), who appears at his most embarrassing moments.