Free Enterprise is a 1998 comedy/romance movie featuring William Shatner, directed by Robert Meyer Burnett and written by Mark A. Altman and Robert Meyer Burnett. The film deals with the mid-life crises of its two main protagonists, Mark and Robert, fictionalized versions of the film's director and producer/writer played by Eric McCormack and Rafer Weigel. The two friends struggle with adult career and relationship problems, all the while defiantly clinging to the geeky science fiction pop culture of their youth and seeking advice from their greatest hero, William Shatner.

Shatner plays a campy caricature of himself as he works on a one-man musical version of Julius Caesar in hopes of finally being taken seriously as an artist. Hip-hop artist "The Rated R", joined by Shatner, provides the concluding musical number, Julius Caesar, a pastiche of famous lines from the play set to a rap rhythm. The film's score was produced by Scott Spock.

The film is laced with references to past and contemporary science-fiction films and television shows, such as Star Wars and Logan's Run. Most prominent is the original Star Trek, which is treated by the protagonists as a source of inspiration and moral guidance. Free Enterprise explores the dating scene for late gen-x Hollywood singles from a decidedly sardonic perspective.

The film won four awards including the 2000 Saturn Award for Best Home Video Release. A new 2-disc DVD special edition Free Enterprise: Extended "Five Year Mission" Edition was released on March 7, 2006.

Young filmmakers (Rafer Weigel, Eric McCormack) trying to hawk a movie titled "Bradykillers" about a serial killer who goes after victims Marcia, Jan, and Cindy meet their screen idol, William Shatner. Shatner, appearing as himself, has fun poking fun at his own image. The two young men, who idolize him and in their fantasies have seen him as a shadowy fairy godfather figure, are alarmed at the reality of the middle-aged non-Captain Kirk man that they meet. However, their relationship helps anchor the two more into reality. Written by John Sacksteder