Norm Macdonald once called this movie "box-office poison" in an interview with Conan O'Brien and Courtney Thorne-Smith in May of 1997, prior to this movie's release.
In a two week limited release, the film opened to 30th place in its opening weekend, grossing $181,233 from 196 theaters (averaging just $925 per screen). In the film's second weekend, it slid down to 54th place, grossing $43,770 from 188 theaters (losing 75% of its gross and pulling in only $233 per screen). The film made a total of $306,715 at the box office.
On their "Chewin' It" Podcast, Steve Lemme and Kevin Heffernan said that Trimark chose to produce this movie over Broken Lizard's movies Puddle Cruiser (1996) and Super Troopers (2001) because executives thought "Chairman" would be more successful. Trimark vice president Phil Goldfine felt Carrot Top had "the ability to become the next Jim Carrey". He also thought Carrot Top had "the potential to become Trimark's tentpole" and that he was "just incredibly funny". Three years after the film, Trimark then became defunct and folded into Lions Gate before it could finance the Broken Lizard projects.
In the same Conan interview, Norm MacDonald made a joke that the 'board' in "Chairman of the Board" is spelled B-O-R-E-D. In the movie, Edison makes kind of the same joke where he says to the boardroom people, "This must be the boardroom... you guys look pretty bored."
Courtney Thorne-Smith recently has admitted that the film is "not a project that is of great pride" for her. After filming, she hoped the film would just "fade away", but she was contractually obligated to promote it. She said she "was so happy" when Norm MacDonald hijacked the Conan interview and started roasting the film because she didn't have much to say about it herself anyway. She did not have a great experience making the film. The only reason why she did the film was she really wanted to do comedy after doing 5 years of drama on "Melrose Place". To this day, Courtney has never seen the film.