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I think the film you may be thinking of is called The Wrong Box: https://en.wikipedia.org/wiki/The_Wrong_Box It's an English comedy from 1966 about a tontine, which is what the arrangement you are describing is called. Here is the trailer: ...


By any chance is it John Waters' Pecker from 1998? Not certain, but some elements sound similar.


Sounds like the Mel Brooks film Life Stinks. I saw it ages ago, so don't remember the exact scene you mentioned, but the premise sounds similar. From IMDB: A filthy rich businessman bets a corporate rival that he can live on the streets of L.A. without the comforts of home or money, which proves to be tougher than he thought. And the trailer: ...


It's 2 Days in Paris with Adam Goldberg and Julie Delpy, who was also the writer and director. Marion and Jack try to rekindle their relationship with a visit to Paris, home of Marion's parents -- and several of her ex-boyfriends.

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