The Great Gildersleeve (1941–1957), was initially written by Leonard Lewis Levinson. He was one of broadcast history's earliest spin-off programs. The character was built around Throckmorton Philharmonic Gildersleeve, an individual who had been a staple on the classic radio sit-com Fibber McGee and Molly. He was first introduced to FMAM on 10/3/39 episode #216. The Great Gildersleeve enjoyed its greatest success in the 1940s.

On Fibber McGee and Molly, Peary's Gildersleeve was a pompous windbag who became a consistent McGee nemesis. "You're a haa-aa-aa-aard man, McGee!" became a Gildersleeve catchphrase. The character was given several conflicting first names on Fibber McGee and Molly, and on one episode his middle name was revealed as Philharmonic. Gildy admits as much at the end of "Gildersleeve's Diary" on the Fibber McGee and Molly series (10/22/40).

Premiering on August 31, 1941, The Great Gildersleeve moved the title character from the McGees' Wistful Vista to Summerfield, where Gildersleeve now oversaw his late brother-in-law's estate and took on the rearing of his orphaned niece and nephew, Marjorie (originally played by Lurene Tuttle and followed by Louise Erickson and Mary Lee Robb) and Leroy Forester (Walter Tetley). The household also included a cook named Birdie. Curiously, while Gildersleeve had occasionally spoken of his (never-present) wife in some Fibber episodes, in his own series the character was a confirmed bachelor.

The key to the show was Peary, whose booming voice and facility with moans, groans, laughs, shudders and inflection was as close to body language and facial suggestion as a voice could get. Peary was so effective, and Gildersleeve became so familiar a character, that he was referenced and satirized periodically in other comedies and in a few cartoons.

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