The first step to becoming a filmmaker is to watch great works then analyze and critique them. I have found these films to be especially effective when teaching storytelling, composition, and editing. Some of these films are Oscar winners, some are not. Many of them are urban cult classics. You can even ask your students to let you know which music videos have been influenced by these works.
Blood In, Blood Out - Three brothers, their choices, the consequences. (also called Bound by Blood)
City of God - Gangs in Brazil. The documentary about Favelas that's on the US dvd is also very educational. A nice contrast is to show this film with Black Orpheus.
The Conversation - A sound tech regrets the job he's done. Coppola directs.
Cooley High/Boyz in the Hood - An African-American High School story. Cooley High is set in Chicago in the 1970's and written by the same guy who co-created Good Times. Boyz in the Hood is essentially a remake/modernized version set in LA in the 80's.
Made in America: Crips & Bloods - This documentary by Stacey Peralta presents valuable perspective and also shows some great CG (After Effects, Motion, etc.) technique.
Do the Right Thing - Great example of issue filmmaking and also had a huge influence on music videos. Shows a wide range of camera angles and moves.
Klute - 1972 Oscar winner about prostitution. Deep. Shows how the camera can be used effectively when NOT moving.
Mi Familia - LA's Chicano history told in a classic Hollywood structure.
Requiem for a Dream/Trainspotting/Gridlock'd - Movies about drug addicts. Three very different takes. A good question to ask is which one is the most realiztic and why?
Scarface - If you have to ask, you'll never know.
To Be and To Have - A beautiful documentary about a group of schoolchildren and their teacher in rural France. In filmmaking, many times simple is better.
Visions of Light - Documentary about the job of the Cinematographer/Director of Photography. Dials in detail that students didn't realize was there.
The Warriors - Cult classic. Everything old is new again.
Be sure to screen all of these films in advance, many of them contain adult language or themes that may not be appropriate to your school/program. However, you can also show a less offensive scene or portion of the film for discussion.
