The Many Loves of Dobie Gillis was a situation comedy which ran on CBS from 1959 to 1963. The television series and some episode scripts were adapted from a 1951 collection of short stories with the same name, written by Max Shulman, that also inspired the 1953 film The Affairs of Dobie Gillis. A followup novel, I was a Teen-Age Dwarf, appeared in 1959.

In the TV series, teenager Dobie Gillis (played by Dwayne Hickman) aspired to have popularity, money, and the attention of beautiful women. He didn't have much of any of these qualities in abundance, and the tiny crises surrounding Dobie's lack of success made the story in each weekly episode. His partner in crime was beatnik Maynard G. Krebs (played by Bob Denver). This program was from Martin Manulis Productions in association with 20th Century Fox Television, creator Shulman also wrote the theme song.

Each episode began and ended with Dobie pondering his problem, posing à la "The Thinker" by Auguste Rodin. In fact, he was usually in a park on a bench with a reproduction of the famous statue immediately behind him.

Dobie's two main antagonists were popular rich kids Milton Armitage (portrayed by a young Warren Beatty) and, after Beatty's departure, Armitage's cousin Chatsworth Osborne, Jr. (played by Steve Franken ), and homely busybody Zelda Gilroy (portrayed by Sheila James ); the former Dobie hated as he had all that Dobie wanted, and the latter Dobie despised because she was hopelessly in love with him and he was annoyed by her advances. Dobie himself was hopelessly attracted to wealthy, distant blonde Thalia Menniger (Tuesday Weld), as well as an endless number of other beautiful women.

As a high school student Dobie still lived at home with his parents in the show's early years, and his interaction with his parents was a source of much of the humor. His mother was very caring and perhaps tended to baby her son a little too much; his father, a grocer, was a very proud, somewhat belligerent World War II veteran who would often, on the slightest provocation, remind his listeners, "I was in the Big One – W W Two!" but was deep down a good and decent man. In later years, Dobie moved on from high school to S. Peter Pryor Junior College, surrounded by many of the same people; in between, he and Maynard (along with Chatsworth) even did a brief stint in the peacetime U.S. Army (Vietnam was still of a minor concern to most Americans when the series ended).

This program, like several others from roughly the same period, was probably more popular as a late-afternoon rerun than it had ever been in prime time and is probably remembered as well as it is for that reason. The program even spawned two sequels, TV pilot Whatever Happened to Dobie Gillis (1978) and TV movie Bring Me the Head of Dobie Gillis (1988). In these, Dobie had married Zelda. In real life, after largely retiring as an actor Dwayne Hickman spent many years as an employee of CBS in the programming department, at one point being its Vice President, and also worked as a television director.