In Fibber McGee and Molly, Peary's Gildersleeve had been a pompous windbag and antagonist of Fibber McGee. "You're a haa-aa-aa-aard man, McGee!" became a Gildersleeve catchphrase. The character went by several aliases on Fibber McGee and Molly; his middle name was revealed to be "Philharmonic" in "Fibber Discovers Gildersleeve's Locked Diary" episode #258 on October 22, 1940.

"Gildy" grew so popular that Kraft Foods—promoting its Parkay margarine—sponsored a new series featuring Peary's somewhat mellowed and always

The Great Gildersleeve premiered on NBC on August 31, 1941. It moves the title character from the McGees' Wistful Vista to Summerfield, where Gildersleeve oversees his late brother-in-law's estate and rears his orphaned niece and nephew, Marjorie and Leroy Forrester. The household also includes a cook named Birdie. While Gildersleeve had occasionally mentioned his (unseen) wife in some Fibber episodes, in his own series he is a confirmed bachelor.

At the outset of the series, Gildersleeve administers a girdle manufacturing company ("If you want a better corset, of course, it's a Gildersleeve"); later and during the remainder of the show he serves as Summerfield's water commissioner. befuddled Gildersleeve as the head of his own family.
The Great Gildersleeve was a happy endeavor where great talent met with great writing. Gildersleeve was invented by actor Harold Peary, who would play him through most of the character's life. However Gildy would also spend time under the stewardship of Willard Waterman. Leonard L. Levinson held the pen during the first season, and created most of the characters that filled Gildy's hometown of Summerfield. However, under the writing of John Whedon the show truly came to life/

Peary's Gildersleeve proved popular enough that it was thought to try the character in his own show. Johnson's Wax, which sponsored Fibber McGee & Molly, sponsored an audition recording for The Great Gildersleeve, and the Kraft Cheese Company signed on as the show's regular sponsor. Gildersleeve was transplanted from Wistful Vista to Summerfield with more than just a locale change—now a bachelor (his character had a never-heard wife on Fibber McGee & Molly), and now the water commissioner instead of the owner of the Gildersleeve's Girlish Girdles company. With much of his pomposity and cantankerousness toned down, he was also newly domesticated and appointed guardian of his orphan niece Marjorie and nephew Leroy. Implicitly well-off though by no means wealthy, Gildersleeve was depicted winding up his lingerie-making company and taking up a new life as Summerfield's water commissioner.

The Great Gildersleeve premiered August 31, 1941,^[3][4] and became a steady hit for the rest of the decade, Peary's sonorous voice and flustered catchphrases ("You're a brii-iii-iight boy, Leroy!" was a modification of his famous McGee catchphrase) among radio's most familiar sounds. Lurene Tuttle played Marjorie; Walter Tetley, a veteran of Fred Allen's Town Hall Tonight cast and other shows, played Leroy; and, Lillian Randolph played Gildersleeve's ego-puncturing maid and housekeeper, Birdie.

The show's humor, like that of McGee, was drawn through clever word-play and phrasemaking as well as Gildersleeve's earnest stumbling and basically warmhearted nature. His new nemesis was Judge Horace Hooker (Earle Ross) ("That crook of a Hooker has hooked our cook!"), who oversaw his guardianship of Marjorie and Leroy and became a friend and periodic rival in various schemes. Periodically, storylines were serialized, such as some of Gildersleeve's romantic interests (especially his aborted marriage plans with Leila Ransom) and political aspirations (he once ran for Summerfield mayor); in time, some of the clever word playing was toned down.

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