Free Enterprise carries a high price

Cover artwork by España Sheriff

Bill Shatner revived his career with Free Enterprise by playing an exaggerated version of himself. But at what cost to the rest of us?

Free Enterprise is a 1998 movie in the tradition of Kevin Smith and other indie 90s romcoms steeped in sentiment and vulgarity. The big draw of the film is Shatner’s portrayal of himself as an addled yet wise muse to Robert and Mark, a pair of lower-end Hollywood worker bees who spend an equal amount of time dropping quotes from classic sci-fi television shows and films, and engaged in problematic skirt-chasing meant to, I dunno, convince the audience these are cool nerds.

But we’re not here to talk about the main characters, at least not yet. Our focus is on Mr. Shatner and what he pulled off by appearing in the film, which is nothing sort of a career miracle.

At the time, Shatner’s career had more or less ground to a halt. The Star Trek films had moved onto the Next Generation crew, Boston Legal was far in the future, and Canada’s finest thespian decided to roll the dice and appear in a strange little geekcentric film which hinged on his presence.

Shatner is by far the best thing about the movie, despite minimal screen time. It’s possible the endless parade of imitators throughout the decades changed our expectations of an actual Shatner performance, but he comes off as a charming, slightly befuddled has-been with nutty ideas about future projects, primarily a hip hop version of Julius Caesar.

He’s also a beacon of civilized discourse in a film full of back and forth jibber jabber between two nerds consumed with self-denial and self-regard. It’s not that Shatner is any more advanced than the average male circa 1999, he’s just older, a better actor and not engaging in wish fulfillment like the two leads (channeling the filmmakers). He also doesn’t seem to care that he’s in a low-rent ripoff of Swingers.

Now, a word about the aforementioned heroes of this piece. Mark, played by future Will and Grace star Eric McCormack, and Robert, played by Rafer Weigel, are two Hollywood sleazedogs, full stop. They’re made out to be heroic geeks just trying to make a stand and push things forward in their lives and careers all while loving the hell out of some Star Trek.

Back in 1998, all we had was Star Trek and The X-Files (yeah yeah, Babylon 5, whatever), and the idea of two characters dropping quotes hither and yon and showing respect for the same things we all loved sounded like a great idea, at least to a niche audience. This was a time when liking geeky stuff was still something you hid or at the very least kept amongst a small group of friends. A film celebrating all the things we loved, and not looking down on them? Sign me up!

But unfortunately, the main characters (and the film itself) look down on women and treat them like sex objects at every turn, and in 2019 it is excruciating to watch. Every time Robert and Mark comes even close to regarding women as something other than a temporary distraction or a chance for furtive sex, they go for the cheap laugh. I like a dirty joke as much as the next person, but the contempt and misogyny is never far from the surface in this movie, and given we live in an age of unbridled online grossness, it leaves a lingering bad taste.

In fact, I’d argue the characters in the film are no different than today’s online trolls and angry YouTube polemicists. They’re crass, gatekeeping clods who think encyclopedic knowledge of TV shows makes up for the gaping holes in their personality, and are openly hostile to anyone who disagrees with them or even enjoys the same things in a different manner. Starting to sound familiar? Just go on the internet for ten minutes and say you’ll like something, and the mutated spawn of Mark and Rob will let you know you are wrong and probably should die.

Back to Shatner. When the film debuted in 1998, it came and went and that was more or less that. Free Enterprise gained a cult following in the years since its release, but I’d argue the biggest beneficiary from the film’s limited success is one Captain James Tiberius Kirk. What notoriety the film had stemmed from Shatner’s role, either because he was working in a weird little indie or because he was willing to satirize himself in a way he never had before.

After Free Enterprise, Shatner went on to record an album with Ben Folds, star in Boston Legal and even leap onto the first (and as far as I know, only) show ever to be spawned from a Twitter feed, $#*! My Dad Says.

He also, legend has it, gained his long-standing role as the spokesperson/mascot of because they’d seen his role in Free Enterprise and liked what they saw. Not bad for a has-been actor doing an indie movie for nerds on a lark.

Though as William Shatner himself once said in song, “better to be a has-been than a never-was”.

Better for him, yes. For the viewers of Free Enterprise… not so much.

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