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Love on a Bet (1936)

Genres: Comedy, Romance

An aspiring theater producer convinces his wealthy uncle to finance a play on the condition that he lives the play’s far-fetched plot: making a cross-country trip with no money.

Gene Raymond as Michael MacCreigh
Wendy Barrie as Paula Gilbert
Helen Broderick as Aunt Charlotte
William Collier Sr. as Uncle Carlton MacCreigh
Spencer Charters as Plaza Ritz Hotel Owner
Walter Johnson as Stephen Dody
Jack Randall as Jackson Wallace
Eddie Gribbon as Donovan, Stupid Escaped Con