Sidewalks of New York (1931)

Wealthy philanthropist Homer Van Dine Harmon (Buster Keaton) resolves to turn one of his tenement houses into a boys' sporting club after falling for Margie (Anita Page), the sister of young hoodlum Clipper (Norman Phillips Jr.). Unknown to both Margie and Homer, the adult leader of a kids' street gang, Butch (Frank Rowan), employs Clipper to pull off several jobs. When Homer declares his feelings for Margie, she insists that she will marry him only if he can save Clipper from a life of crime.