To fully appreciate Buck Benny Rides Again, one must have some familiarity with Jack Benny's radio programs of the 1939-40 season. During this period, Jack's broadcast costars included bandleader Phil Harris, announcer Don Wilson, singer Dennis Day and comedians Eddie "Rochester" Anderson and Andy Devine. All five supporting players appear in this film, all playing "themselves" just as Benny does. Falling in love with aspiring singer Joan Cameron (Ellen Drew), Jack vows to go out of his way to impress her. When he learns that Joan is headed for a western dude ranch, he poses as "Buck" Benny, a rootin'-tootin'-shootin' 100% genuine cowboy. In truth, both Jack and his valet Rochester are terrified at the Wide Open Spaces, certain that they'll be scalped by Indians at the first opportunity, but through a series of silly coincidences Benny manages to convince Joan that he's an honest-to-goodness frontiersman. The plot thickens when a pair of modern-day desperadoes (Ward Bond and Morris Ankrum) plot to rob the dude ranch's safe, but our hero saves both the day and his girlfriend, with the unsolicited but very welcome assistance of his pet polar bear Carmichael (the same bruin who allegedly ate the gas man on Jack's radio show). Benny fans will get an extra kick out of seeing his legendary Maxwell in all its sputtering, backfiring glory, while old-time radio aficionados will enjoy hearing the voices of Mary Livingstone (Mrs. Benny) and Jack's "friendly enemy" Fred Allen. Frank Loesser's musical score includes such hit-parade favorites as "Say It (Over and Over Again)" and "My! My!", the latter sung by Rochester to his sweetie Josephine (Theresa Harris).