Let’s put it simply: this film is (purportedly) the story of how internet pornography came about. It starts out humbly enough: two idiots – Wayne and Buck (played by Giovanni Ribisi and Gabriel Macht) – come up with a great idea on how to quickly acquire new means of satisfying themselves via the internet (“Who pays for stuff on computers? That’ll never work!”) when their old VHS tapes just won’t do. Unfortunately, what begins as an exciting, coming-of-industry tale a la Pirates of Silicon Valley quickly becomes a case of an overly-ambitious film overreaching its grasp.
Quickly realizing that scanning smut magazines and posting the contraband to the internet is a great source of income, but hardly a long-term solution, the duo concludes that they need to start producing in-house content. To that extent, they fall in league with the Russian mafia who are more than happy to produce legions of beautiful women for a cut of the profits. Of course, when Wayne and Buck forget that final point, they end up in a world of hurt that only Jack (Luke Wilson) can save them from. When I think of Luke Wilson, I tend to think of C-grade, direct to video films, which is a shame because in his role here, we see him at his most solid. Jack concludes that the best approach to the whole mess is to build a non-descript corporate entity that discretely governs all these web sites while making a lot of money (hence the somewhat-confusing title “Middle Men”). The problem we quickly encounter is that the script can’t keep track of whose story it’s telling, bouncing between the three characters for half an hour before sailing off the deep end when they accidentally kill the mob boss’s nephew trying to settle their debts.
Jack over-narrates his own arc from fixer-upper to new age pornographer, from successful family man to absentee father, and from the film’s hilarious origin to cringe-worthy conclusion that invokes a textbook-grade deus ex machina to tie everything together. The film meanders, building and dropping sub-plots; establishing tension and then throwing it away on a whim. There’s an interesting tale buried somewhere in here, but the film struggles through its 105 minute length to show it.