Three friends, Nick, Dale, and Kurt, are each suffering under the tyranny of their respective dreadful bosses. Nick has been slaving away for a promotion, but his conniving boss, Dave Harken, dangles the opportunity in front of him only to swindle him and claim the promotion for himself. Dale endures relentless sexual harassment from his boss, Dr. Julia Harris, who threatens to destroy his upcoming marriage if he doesn't submit to her advances. Kurt, on the other hand, revels in his job with a benevolent boss who suddenly dies, leaving his cocaine-addicted son, Bobby Pellit, to take over the company and drive it into the ground with his irresponsible behavior.

Driven to the edge of despair, the trio reaches the conclusion that their lives would be immensely better without their bosses. After a drunken night and inspired by crime movies, they agree that the only way to liberate themselves from their miserable predicaments is to eliminate their bosses. They employ the service of an ex-convict named Motherfucker Jones, who they expect to be a hitman; he instead advises them to kill each other's bosses to avoid suspicion. The friends concoct a convoluted plan filled with surveillance and reconnaissance to ensure their alibis remain intact, but as they fumble through the execution, their ineptitude creates a web of increasingly complicated and unintended consequences.