Steve Hightower (Steve Harvey) is a has-been 1970s Funk legend who is now a music teacher/Vice-principal at Booker T. Washington High in Chicago. Budget cutbacks meant Steve also had to teach drama and art, much to his surprise. Cedric Robinson (Cedric the Entertainer) is a coach at the high school, and Steve's long-time best friend. The principal of Booker T. Washington High is Steve's former classmate, Regina Grier (Wendy Raquel Robinson),
who Steve affectionately calls "Piggy", due to the fact that she was overweight as an adolescent.

Steve seemingly meets his match in a pair of his students: Romeo Santana (Merlin Santana), a stylish, popular, self-absorbed ladies' man, and the equally vacuous Stanley Kuznocki, nicknamed Bullethead (William Lee Scott).

In 1997, the show introduced a new character, a secretary named Lovita Jenkins (Terri J. Vaughn), a woman who is fundamentally good in nature, but nonetheless, considerably unrefined in terms of disposition. Cedric and Lovita begin dating, and eventually marry and produce a child. The show also featured a succession of young actresses who served as female foils to Romeo and Bullethead; the longest-lasting of these was Lori Beth Denberg as the overachieving, socially inept Lydia Gutman. Rapper The Lady of Rage also had a recurring role as Coretta Cox, a physically massive, brutish teenaged girl in romantic pursuit of Romeo.