Dabney Coleman is Otis Drexell, a fifth-grade teacher at fictional Grantwood Elementary School in Cedar Bluffs, Iowa. Drexell was a divorced father living with his two daughters, the boy crazy Melissa (A. J. Langer), who dated happy, dim-witted Slash (Phil Buckman), and the levelheaded, mature Brenda (Brittany Murphy). His sarcastic, cynical and manipulative ways made it easier to deal with his class. Drexell's backstory revealed he was a corporate raider who lost a large amount of money on a failed venture, dodged his taxes, and was arrested. At his sentencing, he was offered a suspended sentence if he served as a teacher at the understaffed school to pay off his back taxes. The cast also included two antagonists, the smug rival teacher Roscoe Davis (Dakin Matthews), who enjoyed putting Drexell down, claiming he had a better class of students, and principal Francine Itkin (Randy Graff), who thought Drexell was incompetent and couldn't control his class. Itkin later had a nervous breakdown and was replaced by shrewd principal Marylin Ridge (Edie McClurg).
One of Drexell's few friends was P.E. teacher George Foster (Cleavant Derricks), who shared Drexell's love of sports and beer. Early episodes focused on Drexell's unwillingness to teach his students lessons by the book, while later episodes focused more on his life outside of school and his attempts to be a good father. On one occasion, Drexell's ex-wife made an appearance; Drexell hoped she would remarry so he could stop paying alimony.
An early episode of the show had a montage of historically accurate flags, from the Red Ensign of Colonial America and showing how the American flag changed, with the current 50-star flag marked "1991" followed by the flag of Japan marked "2000". This had been criticized by Asian-American groups and the Veterans of Foreign Wars who considered that to be a joke in poor taste.