One of radio's first family comedies (and the medium's first "spin-off" series), The Great Gildersleeve began when actor Harold Peary suggested that Fibber McGee and Molly writer Don Quinn create a pompous windbag who could do battle with the braggart McGee.

In 1941, Peary took his portrayal of Throckmorton P. Gildersleeve from Wistful Vista to the small town of Summerfield. In Summerfield, Gildersleeve became city water commissioner, guardian to teenage niece Marjorie (played at various times by Lurene Tuttle, Louise Erickson, and Mary Lee Robb) and wiseacre nephew Leroy (played by Walter Tetley), and employer to housekeeper Birdie Lee Coggins (played by Lillian Randolph). Eventually, Gildersleeve developed friendships with Judge Horace Hooker (played by Earle Ross), barber Floyd Munson (played by Arthur Q. Bryan), and Mr. Peavey, Summerfield's pharmacist (played by Richard LeGrand), who could puncture any of Gildersleeve's arguments with a rueful "Well, now, I wouldn't say that."

Gildersleeve enjoyed a number of romantic entanglements over the years, although the most enduring was his on-again, off-again engagement to southern belle Leila Ransom (played by Shirley Mitchell).

When Peary quit the show in 1950, Willard Waterman took over the title role of The Great Gildersleeve until the show ended in 1957.

The Great Gildersleeve was inducted into the Radio Hall of Fame in 2011.