In 1993, Massee portrayed the character Funboy in the film The Crow, starring Brandon Lee. Massee was the actor who fired the shot that killed Lee by accident on the set in 1993, due to an improperly prepared prop gun. He was so traumatized by the event that he returned to New York and took a year off from acting. He refused to view the film. In an interview in 2005, 12 years after the incident, Massee revealed that he still had nightmares about it, going on to say, "I don't think you ever get over something like that."