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Currently you are able to watch "The Many Loves of Dobie Gillis" streaming on Plex for free.
The Many Loves of Dobie Gillis is an American sitcom that aired on CBS from 1959 to 1963. The series and several episode scripts were adapted from a 1951 collection of short stories of the same name, written by Max Shulman, who had also written a feature film adaptation of his short stories for MGM in 1953, The Affairs of Dobie Gillis. The series revolved around the life of teenager/young adult Dobie Gillis, who, along with his best friend, beatnik Maynard G. Krebs, struggles against the forces of his life - high school, the military, college, and his parents - as he aspires to attain both wealth and dates with girls. The Many Loves of Dobie Gillis was produced by Martin Manulis Productions in association with 20th Century Fox Television. Creator Shulman also wrote the theme song in collaboration with Lionel Newman.