When he was trying to raise funds for the film, Terry Zwigoff encountered Terry Gilliam whom he knew had worked with Robert Crumb in the late 60s. Approaching Gilliam, Zwigoff asked for some help with the budget. Gilliam reached into his pocket, handed over a nickel and then walked away.
Filmed over a period of six years.
According to Robert Crumb, after his brother Charles committed suicide, the first thing his mother said to him was "How could he do this to me?!" Critic Roger Ebert added that after Charles' death, his mother had already thrown out most of his childhood drawings before Robert was able to rescue it.
Director Terry Zwigoff had known cartoonist Robert Crumb for many years before making this documentary about Crumb and his family, as they had found each other through their shared love for 1920s and 1930s music, and had once played in the same band. According to critic Roger Ebert, Zwigoff told him that during his nine-years-long, money-starved struggle to make this documentary, he "called in every favor he owed me" to persuade Crumb to be in the film, all on an average income of about $200 a month. Zwigoff also suffered from crippling back pain at the time and was suicidally depressed, having a loaded gun next to his bed while trying to work up the nerve to kill himself. Ebert later added that the urban legend that Zwigoff threatened to kill himself to get Crumb to cooperate was not true, but suggested that making the film probably saved Zwigoff's life.
Media reports following the film said that Robert Crumb later told Terry Zwigoff that he hated the film. According to Zwigoff, however, this never happened and the two still speak on a regular basis.