This was tough. My answer is really any Wes Anderson film. Its probably because of the style of his films. He always brings his characters close to the viewer. Even before they are presented fully in a film, you immediately know them because they are reflections of everyone's personality. Whether it be an obvious trait that is visible to the public or a hidden shame or secret that defines who we are. "Rushmore" brings these archetypes to life. The setting and stories are not what remind me of a place, its the characters. Throughout life, you meet all sorts of people and each one can be seen in an Anderson film. This is the reason why Wes Anderson films (I guess "Rushmore" mainly) reminds me of my days at CUA and UMBC.