Die lustigen Vagabunden 1940
Overview: On account of a bet, the painter Menzinger and his friend Schratt decide to travel the country as unemployed bums (no doubt, because there were so few unemployed and homeless people in Germany just a few years earlier). For two weeks, they wander around Germany; then they're confused with some robbers and they land in jail. How does it feel to imitate the homeless now, guys?