Aspiring to attain popularity, wealth and the attention of beautiful, money-hungry blondes, luckless teenager Dobie Gillis (Dwayne Hickman) will not be discouraged as he works toward that which he desires. Along with beatnik buddy Maynard G. Krebs (Bob Denver), Dobie carries out his bound-to-fail schemes while trying to get the better of the rich kids and make his parents happy.