Rumble Fish
I must have been poisoned by too much anime in my childhood because the aloof big brother archetype is still the coolest thing in the world to me.
Got the Blu-ray recently so I was especially struck by how beautiful everything is. The fire escape shadows in time lapse really stick out in my mind. Also, I've seen this three times now and never noticed that Patty's sister is Sofia Coppola and the hooker was S.E. Hinton!