50 Million Frenchmen (1931)

Independently-wealthy American Jack Forbes has just arrived in Paris. Because of his wealth he can have any woman on his arm. Currently that role is filled by Marcelle Dubrey, but he ditches her when he spots the woman of his dreams. When Jack tells his equally-wealthy friend Michael Cummins that he will marry that mystery woman, Upon learning that that woman is Lu Lu Carroll, whom he has also been trying to court, Michael bets Jack $50,000 that he can't give up all his money and get engaged to her within two weeks. Jack accepts the bet as Mike strips him of his money. Jack must try to meet and woo her without doing anything with her that requires money, while trying to hide the fact that he has no money as he tries to earn some using his limited job skills. Meanwhile, Michael hires American detectives Simon Johanssen and Peter Swanson to tail Jack to ensure that he keeps to the rules of the bet, but also to thwart Jack's every attempt with Lu Lu. Michael is unaware that these two are poor schmucks who are rather inept at being detectives. The combination of all their issues gets the collective into one misadventure after another as the fortnight wears on.