Middle Men is a 2009 American black comedy-drama film directed by George Gallo and written by Gallo and Andy Weiss. It is based on the experiences of Christopher Mallick, who was previously associated with the internet billing company Epoch and was the founder of ePassporte. Mallick was accused of stealing millions of dollars from his customers at ePassporte to fund the film's development. It stars Luke Wilson, Giovanni Ribisi, Gabriel Macht and James Caan.

In 2004 Houston, Jack Harris leaves home with several million dollars in a duffel bag, to pay Russian mobsters. Harris is worried about the safety of his wife Diana and their children.

Flashback to 1997 in Los Angeles, where Jack helps a sick friend managing a nightclub. Nearby, Wayne Beering and Buck Dolby are best friends renting together. The drug-addicted friends are watching porn movie reels when Wayne asks why there is no porn on the internet. Buck, a former NASA scientist, takes 15 minutes to create a program to allow online credit card transactions to charge people for looking at dirty pictures on their website. They quickly earn thousands of dollars. Needing more porn content they approach Nikita Sokoloff, a Russian mob boss who owns a local strip club; Sokoloff agrees to 25% of their business in return for letting them photograph and film his strippers.

Within a month Buck and Wayne's website is hugely successful. They party in Las Vegas while neglecting payments to Sokoloff. Jack has made the LA nightclub a success and attracts the attention of Jerry Haggerty, a crooked lawyer hired by Wayne and Buck to sort out their problem with Sokoloff. Jack meets the friends and becomes a partner in the business, paying Haggerty $200,000 to get out, knowing Haggerty is under federal indictment and thus a threat to the business.

Sokoloff's nephew comes to collect his $400,000 profit, but when he threatens to kill Jack's family, one of Jack's body guards punches him so hard that he falls dead. Jack and his partners dump the body in the ocean and fabricate a story that Sokoloff's nephew took the money and ran. Sokoloff is skeptical, but agrees to let it pass in return for an increase to 50% of the partnership.

Jack expands the business by dropping their porn site and focusing on the online credit card billing services. They create a billing company called "24/7 billing.com", becoming the titular Middle Men for other internet-based porn providers. The billing business is making hundreds of millions of dollars within a year. Jack becomes addicted to the money, sex and power of his new L.A. lifestyle, spends little time with his Houston family and starts a relationship with porn star Audrey Dawns.

Haggerty, bitter that Jack cut him out of a multimillion dollar partnership, schemes to take over the company. He easily manipulates the foolish Wayne and Buck to work with Denny Z, providing billing services for Denny's numerous child pornography websites.

Audrey's live stream porn site is watched by an international web of terrorists, which the US Government uses to track and arrest or kill the terrorists. The FBI asks for Jack and Audrey's help to expand their terrorist hunt, but Wayne and Buck fear that Jack is meeting with the FBI to turn them in for the murder of Sokoloff's nephew and the child porn. The two confide in Haggerty about killing Sokoloff's nephew, which Haggerty uses to incite Sokoloff to make a move on Jack.