Middle Men

Middle Men (2009) is an American crime comedy-drama directed by George Gallo — watch it online on iFILM. Luke Wilson plays Jack Harris, a straight-arrow Texas businessman who stumbles into a partnership with two hapless inventors who have accidentally built the first online billing system for adult entertainment websites.

The film draws on real events from the early commercial internet. Giovanni Ribisi and Gabriel Macht play the erratic, broke, and surprisingly creative developers whose technology quietly rewired how money moved online. Jack just wanted to help them turn a profit. Instead he finds himself managing the Russian mob (Rade Serbedzija), dodging federal agents, and taking counsel from a lawyer who knows far too much (James Caan). He never stops trying to protect his marriage and his daughters while his professional life turns into something no business school covers.

Gallo wrote Midnight Run, and that same instinct for crime stories with comic friction runs through this one. It is funnier and sharper than its premise suggests. Stream Middle Men (2009) online on iFILM.