Wes Anderson fans will be very familiar with today's Fall movie entry, which many people say is one of his best films. A young Jason Schwartzman kicked off his long association with the director here, along with Bill Murray, who was given one of his best roles. Schwartzman is 15 year old Max Fischer, a semi-psychotic student at the prestigious Rushmore Academy who will do anything to stay there and eventually starts a war with Murray over the attentions of Olivia Williams, a widow they both fall in love with. Even though all the usual Wes Anderson quirks got their seeds planted here, there's something about the characters in this one that help the film feel a little more authentic than his later ones would. I think that's why many consider it his best, but my personal favorite is still The Royal Tenenbaums (I do think his films lost something after he stopped collaborating with Owen Wilson on the screenplays).
Original 1998 Trailer: