Middle Men
In 2004 Houston, Jack Harris drives with several million dollars in a duffel bag to deliver to Russian mobsters, worried about the safety of his wife Diana and their children. In 1997 Los Angeles, Jack helps a sick friend co-managing a nightclub. Wayne Beering and Buck Dolby are best friends renting together. The drug-addicted friends are watching porn 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 porn on their website. They earn thousands of dollars in a matter of days. Needing more porn they approach Nikita Sokoloff, a Russian mob boss who owns a local strip club, who agrees to 25% of their business in return for letting them photograph and film his strippers.
Buck and Wayne's website is successful and they party in Las Vegas while neglecting to make 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 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 his head 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 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 what has become a multimillion-dollar partnership, schemes to take over the company. He 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.
When Jack finds out that his partners are helping facilitate Denny Z's child porn, he confronts Denny Z at a house party. Jack sees Audrey having sex with two men at the party and realizes how much he misses his family, leading him to break up with Audrey.
An FBI agent, appreciative of the help Jack has given the government, warns him that 24/7billing.com is about to be indicted for supporting child porn. Jack's life is further complicated when Sokoloff's men kidnap his maid's son, who they believe is Jack's son. Jack gathers up several million dollars and goes to meet Sokoloff, as seen at the start of the film.
Jack is told that the boy will be released if he signs a contract giving his partnership share to Wayne, Buck, Sokoloff, and Haggerty. Jack signs the agreement but backdates it to before Denny Z's child porn business was added. Sokoloff kills Haggerty, but lets Jack go as thanks for all the money he has made him.
The movie ends with Jack's FBI friend charging Sokoloff, Wayne and Buck with providing billing services for child porn. Jack and the maid's son return home, where Diane welcomes Jack back.
murder, flashback