Luke Wilson wears a Rolex Submariner Date

Somebody had to figure out how to charge a credit card on the internet, and George Gallo's Middle Men tells the story of the guys who did it, mostly through internet porn. The film is based on the real experiences of producer Christopher Mallick, who helped pioneer online payment processing in the late 1990s. Wilson plays Jack Harris, a straight-arrow Houston businessman who arrives in Los Angeles to sort out the financial mess made by two chaotic partners, a hopped-up ex-veterinarian (Giovanni Ribisi) and an ex-NASA techie (Gabriel Macht), and ends up building their operation into a fortune. James Caan plays the sleazy lawyer who pulls him in, Rade Serbedzija is the Russian gangster, and the whole thing plays like Boogie Nights crossed with a dot-com cautionary tale.

Harris is the calm center of a story full of people losing their minds over money, drugs, and access. The watch on his wrist has never been reliably identified, which is a small irony in a movie where everyone keeps score in money and status. The picture barely reached theaters anyway: a limited 2010 release that grossed well under a million against a reported twenty-million-dollar budget, with a cast that reads better on paper now than it did then, before Macht spent nine seasons on Suits.