From the UBUWEB feed of plenty I just happened upon this short film by Francis Thompson, which might be what The Cabinet of Dr. Caligari (1920) would have looked like if it was filmed in Manhattan in 1957. Or, as the UBUWEB editors describe it:
This 1957 color film by Francis Thompson turns everyday street life into a surreal kaleidoscope, distorting, fracturing, and multiplying familiar images into a truly original visual experience. (15 min.)
It is a wild film and images likes the samplings below which quickly burn themselves onto the imagination.
Download NY, NY: A Day in NY (1957)