Bringing Up Bobby is the story of a European con-artist and her son Bobby, who find themselves in Oklahoma in an effort to escape her past and build a better future. Olive and Bobby blithely charm their way from one adventure to another until Olive's criminal past catches up with her. Consequently, she must make a choice: continue with a life of crime or leave the person she loves most in an effort to give Bobby a proper chance in life.

Having had a one night stand with an obsessive inmate, the college professor teaching his prison literature class soon lives the nightmare of her decision.

Ben Healy and his social climbing wife Flo adopt fun-loving seven year old Junior. But they soon discover he's a little monster as he turns a camping trip, a birthday party and even a baseball game into comic nightmares.