The Many Loves of Dobie Gillis (also known as simply Dobie Gillis or Max Shulman's Dobie Gillis in later seasons and in syndication) is an American sitcom starring Dwayne Hickman that aired on CBS from September 29, 1959, to June 5, 1963. The series was adapted from the Dobie Gillis short stories written by Max Shulman since 1945 and first collected in 1951 under the same title as the subsequent TV series, which drew directly on the stories in some scripts. Shulman also wrote a feature-film adaptation of his Dobie Gillis stories for Metro-Goldwyn-Mayer in 1953, titled The Affairs of Dobie Gillis, which featured Bobby Van in the title role.

Hickman in Dobie Gillis was among the first leads to play a teenager on an American television program. Dobie Gillis broke ground by depicting elements of the contemporaneous counterculture, particularly the Beat Generation, primarily embodied in a stereotypical version of the "beatnik," mainly in the character of Maynard G. Krebs, portrayed by actor Bob Denver. Hickman wrote in 1994 that Dobie represented "the end of innocence of the 1950s before the oncoming 1960s revolution."

The series revolved around teenager Dobie Gillis (Dwayne Hickman), who aspired to have popularity, money, and the attention of beautiful and unattainable girls. He did not have any of these qualities in abundance, and the tiny crises surrounding Dobie's lack of success made the story in each weekly episode. Also constantly in question, by Dobie and others, was Dobie's future, as the boy proved to be a poor student and an aimless drifter.

His sidekick and best friend was American television's first beatnik, Maynard G. Krebs (Bob Denver), who became the series's breakout character. An enthusiastic fan of jazz music (with a strong distaste for the music of Lawrence Welk), Maynard plays the piano and bongos, collects tinfoil and petrified frogs, and steers clear of romance, authority figures, and work (yelping "Work?!" every time he hears the word). Always speaking with the vernacular and slang of the beatniks and jazz musicians he admired, Maynard punctuates his sentences with the word "like" and has a tendency towards malapropisms. The main running gag on Dobie Gillis would have Dobie or one of the other characters rattling off a series of adjectives describing something undesirable or disgusting ("I'd be a ragged, useless, dirty wreck!"), at which point a previously unseen Maynard would appear (entering the scene in close-up), saying "You rang?"

Dobie Gillis is set in Central City, a fictitious city in the Midwestern United States (the original short stories are explicitly set in the Minneapolis–Saint Paul area). One of the show's running gags is that Maynard is going downtown "to watch them knock down the old Endicott Building" (which is in Saint Paul, Minnesota). Another running gag is the reference, especially by Maynard, to a film called The Monster that Devoured Cleveland and its sequels, one of which always seems to be playing at the local cinema.

Dobie's often apoplectic father, Herbert T. Gillis (Frank Faylen), owned a grocery store and was only happy when Dobie was behind a broom. Dobie's mother, Winifred (Florida Friebus), was a usually calm and serene woman who protected Dobie to the best of her ability and tended to baby him. Herbert Gillis, a proud, hard-working child of the Great Depression and World War II veteran, was often (during the first season of the show) heard to declare, in relation to Dobie, "I gotta kill that boy, I just gotta!" The Gillis family also originally included an older son, Davey Gillis (portrayed by Dwayne Hickman's own older brother, Darryl Hickman), who made three appearances during the first season while home on break from college before being written out of the show.

Dobie's two main antagonists were rich kids Milton Armitage (played by Warren Beatty), who appeared in five episodes, and after Beatty's departure, Chatsworth Osborne Jr., Milton's cousin (played by Steve Franken). Both characters represented the wealth and popularity to which Dobie aspired, but also served as romantic and competitive rivals for Dobie. Beatty's Milton was taller, better looking, and more athletic than Chatsworth. Doris Packer played Clarissa Osborne, Chatsworth's overbearing and snobbish mother, whom he affectedly referred to as "mumsie."

Dobie was hopelessly attracted to the beautiful but greedy blonde Thalia Menninger (Tuesday Weld). Thalia was written out of the series after the first season and was succeeded by a seemingly endless stream of women for whom Dobie hankered. Weld returned as a slightly wiser Thalia for two guest appearances in seasons three and four.