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Middle Men is a 2009 biographical black comedy-drama film directed by George Gallo and starring Luke Wilson, Giovanni Ribisi, and Gabriel Macht. The film is set in the late 1990s and follows Jack Harris (Luke Wilson), a family man and successful businessman who finds himself in the middle of an internet pornography business. The film begins with Jack Harris as a successful businessman who has built his fortune by creating telecommunication deals. Despite the success, he is looking for something new and exciting. One day, he receives a call from Wayne Beering (Giovanni Ribisi), a drug-addicted tech genius who has created a successful pornographic website that he wants to expand. Wayne's partner, Buck Dolby (Gabriel Macht), is a suave and wealthy businessman who manages the operations side of the business. Jack is intrigued and agrees to meet them.

Jack's initial encounter with Wayne and Buck sets the stage for a wild and unpredictable ride. The duo's internet porn enterprise has taken off, but they can't collect payment from subscribers. Jack immediately sees an opportunity to be their business mediator and help them monetize the site.

As Jack gets more involved with their business, he finds himself caught up in a world of sex, drugs, and money. The exhilaration of the business becomes all-consuming, and Jack begins to neglect his family and ethical code. Along the way, Jack realizes that the reason he got involved in the porn business was not because of the money, but rather because of the thrill of doing something new and exciting.

As the business grows, so does the danger. The trio runs into a group of unscrupulous Russian gangsters who demand a cut of their profits. Jack decides to take matters into his own hands and sets up a way to transfer the money to the Russians without involving Wayne and Buck. However, his plan goes awry, and soon Jack finds himself in the middle of an FBI investigation.

Middle Men is a fast-paced, entertaining story that realistically portrays the world of pornography and the internet in the late 1990s. The film manages to touch on the moral and ethical dilemmas that arise from the porn industry without staging a moral crusade against it. The story is well written, and the dialogue is snappy, making for a thoroughly engaging experience.

The performances are fantastic, with the three leads each bringing their unique charisma to the table. Luke Wilson shines as Jack Harris, a man who is trying to resist the temptations of the porn industry while still being drawn to its thrill. Giovanni Ribisi is a standout as the eccentric and drug-addled Wayne Beering, who is the driving force behind the business. Gabriel Macht is also effective as Buck Dolby, the suave and shark-like businessman who can handle the logistics of the porn industry.

The film is also visually stunning. Director George Gallo uses a range of creative angles and filters to evoke the feeling of the late 1990s internet. The scenes showing the online subscription system and the website's design are particularly impressive. The film's soundtrack is also a joy to listen to, with a mix of classic and modern songs that perfectly suit the mood of each scene.

In conclusion, Middle Men is an excellent film that combines humor, drama, and entertainment to tell a story that is both engaging and thought-provoking. The performances, writing, direction, and cinematography all come together to create a film that is not only entertaining but also a fascinating observation of the pornography industry's early days on the internet.

Middle Men is a 2010 drama with a runtime of 1 hour and 45 minutes. It has received moderate reviews from critics and viewers, who have given it an IMDb score of 6.8 and a MetaScore of 60.