Kevin, Danny Masterson, Brian, Ben Crowley, Chris, Darick and Eddie Thomas Ian Nicholas are childhood friends from a working-class neighborhood in Pittsburgh. They are in their mid-20s, working low-paid blue-collar jobs, and dipping into small-time crime like selling marijuana or illegally providing liquor for parties.
Brian convinces all but Eddie to try their hand at pandering, starting with two girls, Bijou Phillips as Jasper and Alexandra Breckenridge as Sienna, and the operation soon grows to include five women. They locate a drug dealer, Ving Rhames as Drug Dealer, to supply cocaine, initially for the girls and then for their clients as well. As the money rolls in, the flashy lifestyle begins to reshape their tastes and priorities, especially affecting Brian, who starts to rely on the drugs himself despite the dealer’s warnings not to partake.
A night of danger unfolds when Chris takes Sienna to meet an old client who is attracted to her. Both end up using crack, and the client murders Sienna. The police arrive, arrest him, and detain Chris, who is outside the room unaware of the crime. He faces multiple charges—prostitution, drug dealing, possession, and more—and could spend years in state prison. Brian visits Chris in jail, where he learns the cops might cut a deal to two years if Chris reveals where the drugs originated. Brian urges Chris to talk, arguing Nate will hunt him down anyway, but Chris is determined to protect the network.
Back with the group, the others decide they won’t continue the business while Chris is jailed and Sienna is dead, and Kevin even reveals that he loves Jasper. Brian then informs Nate about what happened, prompting Nate to hire an old convict to kill Chris in jail. The attempt fails, and Chris turns informant to the police, exposing Brian’s drug-and-pimping operation.
Darick is killed by Nate, and Brian attempts to kill Kevin but fails. Kevin flees the country, with Jasper catching up to him after being shot by Brian in an attempt to slow them down. She survives and catches the next flight out, heading toward treatment or sanctuary. The authorities raid Brian’s luxury penthouse, where he tries to destroy his drug money and flush the drugs away, only to have the water supply cut, preventing him from drowning the evidence. A police helicopter hovers over the deck, and the standoff ends with Brian surrendering his weapons. In a final twist, Nate shoots Brian from a distance with a sniper rifle, preventing him from naming Nate or the rest of the operation. The shooting remains unseen by the cops, who assume a fellow officer took the shot, and Nate’s fate is left ambiguous.
At Darick and Brian’s funeral, Brian’s mother stands with Eddie—who is now in a wheelchair in prison—and Chris, still incarcerated, reflecting on the aftermath. In Eddie’s memories, he reveals that Kevin and Jasper are somewhere outside the United States, and that the “organization” had pulled in over seven million dollars in roughly a year, only to lose it all. He closes with a somber meditation: although his friends briefly lived large, they ultimately “flew off the bridge to nowhere.”
