Mr. Washington Goes to Town (1941)

While reading the newspaper in his jail cell during his stint as a "guest of the county", Wallingford reads a story that his cellmate, Schenectady, has inherited a hotel from an uncle who has recently died. Upon hearing the news, Schenectady falls asleep and dreams of what kind of life he'll lead now that he owns a hotel. It turns out he has a surprise in store.