Lily and Jim (1997) is a 16mm animated short film by Don Hertzfeldt. It is Hertzfeldt's third student film from UC Santa Barbara, for which he single-handedly animated over 10,000 drawings. In the film, an awkward blind date between a hopeless couple goes from very bad to much worse. Voice actors Robert May (Jim) and Karin Anger (Lily) improvised a number of their dialogues.
The movie eventually received 25 film festival awards, including Grand Prizes from the New Orleans Film Festival and the USA Film Festival.
In 1998, it was shown on an episode of MTV's Cartoon Sushi.
In 2005, the original 16mm negative was digitally restored and remastered for the first time, for release on the extensive "Bitter Films Volume 1" DVD compilation of Hertzfeldt's 1995-2005 films. Special features created for Lily and Jim include Hertzfeldt's original production sketches and notes, as well as a 15 minute animatic consisting of humorous audio outtakes and unused improvisational dialogue from the original 1996-97 session tapes. The original voice actors were also reunited after 9 years to do a retrospective audio commentary.
The DVD is available exclusively at the Bitter Films website, http://www.bitterfilms.com