Tim Robbins touted this project around the various studios for six years. Ironically, for a film about the American political process, it was the English production company Working Title that came up with the necessary funds.
The first three albums by Bob Roberts - The Freewheelin' Bob Roberts, Times Are Changin' Back, and Bob on Bob - were spoofs of/based on/homages to Bob Dylan's classic albums The Freewheelin' Bob Dylan, The Times They Are A'Changin' and Blonde On Blonde, respectively, including the cover photos on the first two.
This film was Tim Robbins directorial debut. His friend Helen Hunt appeared in it in a brief cameo as a television news reporter. When Hunt made her feature directorial debut with Then She Found Me (2007), Robbins returned the favor and appeared briefly as one of the interviewees on the Bette Midler character's talk show.
The "Cutting Edge Live" TV show segment is shot at WQED's studio in Pittsburgh, home of Mister Rogers' Neighborhood (1968). King Friday's castle can be seen in the background as the production assistant storms across the soundstage to cut the power. When Fred Rogers was awarded the Lifetime Achievement Emmy Award for Daytime Television in 1997, Tim Robbins was the presenter.
Writer/director/actor Tim Robbins wrote a song called "Revape Amerika" for Tapeheads (1988). It was performed by Robbins, credited as "Bob Roberts". Robbins reworked the song into "Retake America", used in this film.