The Iron Giant (1999)
Director: Brad Bird
Stars: Eli Marienthal, Jennifer Aniston, Harry Connick Jr., Vin Diesel, Christopher McDonald, John Mahoney
Budget: $50-$70 million
Domestic Box Office Gross: $23.2 million
Director Brad Bird is best known for his Pixar films and his work on The Simpsons, but before making The Incredibles and Ratatouille, he made this heart-breaking gem.
A love letter to the monster and sci-fi B-movies of the 1950s, The Iron Giant is about a boy and his robot friend. They have grand, frolicking adventures until the military intervenes. What happens next never fails to turn viewers into puddles of hiccuping sobs. They just don't make cartoons like this anymore, and its failure at the box office is probably why.