The Many Loves of Dobie Gillis is a classic sitcom of the late 1950s. If on the surface the show seems unassuming and standard early sitcom fare, just below the surface is a show that breaks new ground in television. Two significant aspects set it apart from the other shows of that era and make it watchable and influential well into the 1990s. First is the show's focus on teenagers. Second is the addition of a new type of character in the form of Maynard G. Krebs, the outsider.

Dobie Gillis is a teenager in small-town America; the plot revolves around Dobie's life and thoughts. In the course of the show Dobie graduates from high school, briefly joins the army, and returns to the same town to attend college. The show was adapted from Max Shulman's short stories of the 1930s and was updated for the...