On paper, Middle Men, directed by Bad Boys and Code Name: The Cleaner screenwriter George Gallo, is a fascinating (and purportedly true) story about the frontier days of the Internet. A string of fortunate events finds Jack Harris (Luke Wilson), a wholesome entrepreneur from Texas, coming to the aid of Wayne Beering (Giovanni Ribisi) and Buck Dolby (Gabriel Macht). These two geniuses have designed a revolutionary way to sell people pornography over the Internet simply by being the middle men who push a string of credit card numbers from one place to another. They become multi-millionaires in a matter of weeks.
Trouble is these two geniuses are actually complete morons and therefore Jack steps in to partner with the dysfunctional duo. Sorting out their business woes amidst their own clashing personalities is the least of Jack's worries, though, since the duo has also entered a partnership with a Russian gangster, Nikita Sokoloff. And thus begins an unbelievable, too-crazy-to-be-true chain of events that draws Jack from one ludicrous scenario to another.
If you lay out that chain of events on paper, there is no doubt a genuinely interesting story in there. Unfortunately that story of rich men behaving badly would make for an ideal four-page article in an issue of Maxim; it does not necessarily make for a worthwhile feature film.
The systemic problem with Middle Men is that Gallo and co-screenwriter Andy Weiss haven't written a single palatable or interesting character into the picture. Jack Harris is supposed to be the reasonable one, the sensible brain navigating the tumultuous waters Wayne and Bruce stir up, but as the run time wears on, we realize his character is just as poor a decision-maker as the two who got him into the mess in the first place. He's just a sponge. There's no agency in his life, he drifts from one plot point to the next, soaking up everyone else's problems along the way.
As a result, about midway through the film, the one character the audience is supposed to be sympathetic toward has become as obnoxious as everyone else around him. That's no easy feat, either, considering that Wayne and Bruce make Beavis and Butthead look like Rhodes Scholars. The sheer magnitude of how annoying their personalities are is pure tribute to how talented Ribisi and Macht are; it's just a shame that their only purpose in the film is to turn the buffoonery dial to 11. The same goes for the rest of the cast as well. Everyone does a fine job in their respective roles, particularly James Caan as a slimy lawyer and Rade Serbedzija as the psychotic Russian gangster, but the material never challenges them to deliver anything more complex than an on-the-nose performance.
The script also has a remarkable disregard for any desire to teach a lesson, moral or historical, to either its characters or its audience. I suppose Gallo and Weiss can get away with this under the guise that they are simply telling the "true story" of Middle Men producer Christopher Mallick, but the script fumbles every opportunity to take advantage of the nature of film. Instead of using the power of the big screen to tell a story in a way that only movies can, Gallo bogs everything down by just flat out ... telling the story. The over-reliance on Luke Wilson's narration to fill in all of the gaps is staggering to the point where you just want to tell him, as you would a rude member of the audience, to shut the hell up during the movie.
By the time the credits roll you'll be wondering why exactly Middle Men exists as a film. Is it to peel back the curtain on a moment in time that few people know about? No, it's too light on the details for that to be the case. Is it to show how good men can be easily corrupted by just filling their bank accounts? No, because it has no character arc; aside from a few bruises here and there, Jack pretty much walks through the raindrops. Is it to get in on young male fantasy films that are about luxurious lifestyles, overnight millions, and a "you too can date a porn star" mentality? Absolutely.
There's nothing inherently wrong with that motivation, it's why films like The Hangover and shows like Entourage are so popular. But even when those tales are at the height of their "I can't believe this is happening to us!" fantasies, they never forget that the audience has to like the characters and care about what happens to them. In Middle Men's defense, the film never forgets that crucial aspect of storytelling; it just never learned it in the first place.