Went with Some Like It Hot, I love it for its comedic moments, for its complexity in the plot, and for the performances of the actors.
I think is fair to say that this film has as much history as Gentlemen since the actors already had cemented careers and this film acts as a time capsule. I also think there is a huge amount of praise to be given to a film that doesn't need to apologize for being "from a different time." I didn't really appreciate how ahead of its time Some Like It Hot was until listening to this episode. Thanks guys!