Gaily, Gaily (1969)

To escape sinful impulses, Ben Harvey, a callow youth, leaves his small town for Chicago in 1910. A pickpocket promptly relieves him of his money, and he nearly starves before Queen Lil takes him under her wing, gives him a room in her high-class bordello, and gets him a job at a newspaper. He's so sweet and dumb, he thinks Lil's is a boarding house. He's soon caught up in an electoral struggle between a secretly corrupt reformer and an openly corrupt councilman. Can Ben expose corruption or will he be caught up in allure of power? An alcoholic investigative reporter and the bordello's ingénue try to help him grow up.