It's in the Bag (1945)

Based on the popular Russian novel The Twelve Chairs, this stars Fred Allen as flea-circus impresario Fred Floogle. Learning that he's inherited $12 million from his uncle, Fred also discovers that the money has been stuffed in one of thirteen chairs that he's sold at auction. The rest of the film goes off on any number of hilarious tangents, each tied-in ever so tenuously to the plot. Included is an episode at the movies (Fred and his wife Binnie Barnes are continually escorted up several balcony steps and out several alleyway doors), a visit to Floogle's radio cohort Mrs. Nussbaum (Minerva Pious), a brief misadventure with Jack Benny (this time Benny has a hat-check girl in his hall closet, so that he can collect tips from visitors), an impromptu barbershop quartet session with Fred, Rudy Vallee, Don Ameche and Victor Moore, and a confrontation with the dreaded William Bendix mob (Bendix isn't really a gangster; he simply inherited the mob from his mother). Also weaving in and out of the proceedings are John Carradine as a crooked attorney, Robert Benchley as Fred's pompous in-law-to-be, Sidney Toler as a popcorn-munching detective, and Jerry Colonna as Fred's live-in psychiatrist. Two versions of this film exists, one without Fred Allen's ongoing voice over narration. ~ Hal Erickson, Rovi