Ryan

From the video description: "Ryan" is based on the life of Ryan Larkin, a Canadian animator who, 30 years ago, produced some of the most influential animated films of his time. In the film, we hear the voices of prominent animators and artists discussing Ryan's work, and from waitresses, mission-house caretakers and homeless people who make up Ryan's life. These voices speak through strange, twisted, and disembodied computer-generated characters--which combine to reflect the film's creator, Chris Landreth. In the words of Anais Nin, "We don't see things as they are. We see things as we are."

First saw this at the end of my senior year in high school, the year it won the Oscar for best short animated film. Ryan Larkin himself received renewed attention following this film's success, and gave up some of his bad habits to briefly resume his career in animation before dying of lung cancer in early 2007.