Middle Men

Middle Men

Year: 2010

Runtime: 105 min

Language: English

Director: George Gallo

Budget: $20M

DramaComedyCrime

Texas businessman Jack Harris's life takes an unexpected turn when he partners with Wayne Beering and Buck Dolby, plunging him into the burgeoning online pornography industry. As Jack attempts to balance his business ventures with maintaining a respectable image and salvaging his family life, he finds himself increasingly caught up in a complex and morally questionable world. The experience tests his values and threatens to unravel everything he holds dear.

Warning: spoilers below!

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Timeline – Middle Men (2010)

Trace every key event in Middle Men (2010) with our detailed, chronological timeline. Perfect for unpacking nonlinear stories, spotting hidden connections, and understanding how each scene builds toward the film’s climax. Whether you're revisiting or decoding for the first time, this timeline gives you the full picture.

1

1997: Jack teams up with Wayne and Buck and starts the Sokoloff-backed venture

In Los Angeles, Jack helps run a sick friend's nightclub, setting the stage for his future ventures. Wayne Beering and Buck Dolby are introduced as ambitious but impulsive partners who quickly push an online porn idea. They win Nikita Sokoloff's backing by offering him a 25% stake in exchange for filming the strippers.

1997 Los Angeles
2

Sokoloff's nephew arrives to collect profits; a body ends up in the ocean

Sokoloff's nephew comes to collect his share and threatens Jack's family. One of Jack's bodyguards punches him, and he dies. They dump the body in the Pacific Ocean off Los Angeles and fabricate a story that he took the money and ran; Sokoloff accepts the cover-up but demands a bigger stake.

1997 Pacific Ocean (off Los Angeles)
3

Haggerty exits the partnership with a payout

Jack pays Haggerty $200,000 to get out of the partnership; Haggerty is already under federal indictment, making him a liability for the business. Jack aims to keep the venture clean and protect the growing operation from legal trouble.

1997 Los Angeles
4

Sokoloff increases his stake to 50% after the nephew incident

Sokoloff remains wary but is mollified by the cover-up and agrees to raise his share to 50% of the partnership. The balance of power tilts in his favor as the operation expands.

1997 Los Angeles
5

The business pivots to online billing: 24/7Billing.com

Buck and Wayne pivot from running a porn site to building an online billing service, founding 24/7Billing.com. The new model becomes the backbone for a large network of online porn providers. Within a year, the billing business earns hundreds of millions and redefines the players' lives.

1997-1998 Los Angeles
6

Jack sinks into wealth and party life; romance with Audrey Dawns begins

Jack becomes addicted to money, sex, and power, spending little time with his Houston family. He begins a relationship with porn star Audrey Dawns, further entrenching himself in the LA lifestyle. The personal cost of his new life begins to mount.

late 1990s Los Angeles
7

Haggerty schemes to retake control with Denny Z

Feeling sidelined, Haggerty manipulates Wayne and Buck into working with Denny Z, supplying billing services for Denny’s numerous child-pornography sites. The plot thickens as internal tensions threaten the partnership.

late 1990s Los Angeles
8

Audrey's live stream draws terrorists; FBI asks for help

Audrey's live-stream porn site is monitored by an international terrorist network, attracting the attention of the US Government. The FBI asks Jack and Audrey to assist in expanding their counter-terrorism efforts. Wayne and Buck fear Jack will turn them in if the FBI gets too close.

late 1990s Los Angeles
9

Maid's son kidnapped; Jack travels with millions to meet Sokoloff

Sokoloff's men kidnap the maid's son, believed to be Jack's, pressuring Jack to assemble millions and travel to meet Sokoloff. The sequence is shown early in the film, establishing the high-stakes stakes behind the partnership.

2004 Houston
10

Sokoloff shoots Haggerty and lets Jack go

In a brutal turn, Sokoloff shoots Haggerty dead but spares Jack, rewarding him for the money and maintaining the alliance. The shaken partners realize the cost of their lucrative arrangement.

2004 Los Angeles
11

FBI charges Sokoloff, Wayne, and Buck; Denny Z turns state's evidence

The FBI indicts Sokoloff, Wayne, and Buck for providing billing services for child pornography. They begin cooperating with authorities and turn state's evidence against Denny Z, resulting in a reduced sentence for Denny. The network begins to unravel as legal pressure mounts.

2004 Los Angeles
12

Sokoloff flees the country; rumors place him in Moscow

With the case collapsing, Sokoloff faces mounting pressure and flees the country. Moscow is rumored to be his new base as investigators close in on the remaining partners. The future of the operation becomes uncertain.

2004 Moscow
13

Jack returns home; Diane welcomes him back

After the turbulent chain of events, Jack returns to his family in Houston. Diane warmly welcomes him back, signaling a fragile return to normalcy and the end of the immediate crisis. The film closes with a sense of regained, if uneasy, domestic stability.

2004 Houston

Last Updated: October 09, 2025 at 15:40

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Middle Men Summary

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