Preston Sturges - Sullivan\'s Travels (1941)

After years of kowtowing to studio executives by making light, fluffy fare, successful and talented movie director John L. Sullivan wants to make a "message" movie, specifically about the plight of the downtrodden in society. Beyond wanting him to continue making money-making escapist movies, the studio executives counter that his privileged background disqualifies him to make a film about the downtrodden. So Sullivan decides to hit the road with only 10¢ in his pocket to truly experience what being poor is like. The studio executives will only allow him to do this if they can follow him and document his experience. Not wanting it to be a publicity stunt, Sullivan makes a deal with his tailing party: leave him alone for a few weeks, then they'll meet up at a determined location. After a few false starts where he can't seem to shed his privileged past, Sullivan manages to hit the road, this time with an aspiring but struggling actress who believes she can help him navigate road life; he met her when she did a Good Samaritan deed for him. But when Sullivan tries to do his own Good Samaritan deed in return, he finds that shedding his downtrodden life may be even harder than shedding his privileged life.