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Singer Kay Starr and actor Jackie Coogan appear with Red Skelton in the comedy sketch "The Booze Man of Alcatraz." During the Prohibition Era, bootlegger San Fernando Red (Skelton) is sprung from jail on condition that he confine his liquor-brewing activities to the speakeasy run by mobster Frank Nutti (Coogan). Though set in 1927, the sketch is full of anachronistic references to Dean Martin and Elizabeth Taylor. The single funniest moment finds nightclub singer Kay Starr asking San Fernando how they're going to get out of their present predicament, to which he replies, "I dunno, but if we don't, twelve months from now we'll have been dead a year." In the Silent Spot, Red plays a court jester who risks losing his head if he can't put a smile on the face of a melancholy king (Coogan). Musical highlights on this broadcast from October 16, 1962, include Kay Starr's renditions of "You're Nobody Til Somebody Loves You", "Nobody", and "Side by Side".