Considered one of the first avant-garde films in the United States, Manhatta (1921) is essentially a series of random images strung together to create an imaginary day in New York City. The Vanishing Street (1962) documents the disappearance of the Jewish community in London's East End, as old buildings become targets for wrecking balls and are replaced with high-rise housing. Hmm, sounds familiar!
The final short is urban planner William H. Whyte's The Social Life of Small Urban Spaces (1980). Whyte walks the viewer through various small urban parks and plazas to find out where people sit, what attracts people to certain common areas, why we're hesitant to venture to places on foot, and it proposes a city where walking could be rediscovered in the spirit of "drift and détournement" -- the act of wandering the city according to no set route or schedule, immersing oneself in the streets without really going anywhere, and -- gasp -- actually interacting with people! Check it out, and make sure you bring a blanket or chair to sit on. Walk there if you have to.