Willard is an overworked, underpaid chauffeur who works for a mean-spirited pie heiress named Mrs. Crock, just as his father did before him. All Willard wants for Christmas is a new uniform, since the one he wears is the very same he’s buried in, but Crock responds with a cheap pair of cuff links and a pie, while showering lavish gifts on her business partner Chip Oswald and her prized dog Muffin. At the end of a long day, Willard and his best friend Rusty, who runs a local chicken restaurant, hatch a plan to kidnap Muffin and demand a $1,000,000 ransom. Muffin attacks, leaving behind a trail of destruction and blood, the plan collapses when the dog slips away.
Crock and the Pittsburgh police misread the hastily written ransom note and assume Willard has himself been taken. Crock balks at paying at first, until public protests led by Willard’s on-again, off-again girlfriend Hillary pressure her. A second scheme forms: Willard films a fake ransom video and leaks it to the media to force Crock to come up with the money to protect her image as a kind, grandmotherly figure. The plan involves Willard mugging his boss during the ransom drop and leaving a dead body dressed as Willard to mislead the authorities. They enlist Grover Cleaver, a creepy morgue employee, to source a suitable corpse and set up a midnight meeting in a park.
That plan spirals out of control too. Willard does manage to obtain the money, but two small children ambush him with a taser and a shiv and steal the briefcase. Police arrive to find him beaten and taken to a hospital, while investigators locate the dead body that was meant to stand in for him. Willard claims the body was his captor, but the police remain suspicious—Grover used the body of an old homeless dwarf, and Willard insists he was “more ferocious when he was alive.” Returning to work for Crock, Willard learns that she says he now owes her the ransom as well. A mother of one of the attackers returns the briefcase, much to Willard’s relief, and he and Rusty fantasize about a vacation, only to discover the case contains newspaper and cabbage.
During interrogation, Rusty reveals a nervous habit of smashing objects with a desk lamp. The investigation shifts toward Grover, who responds by kidnapping Mrs. Crock while waiting for his cut of the money. Willard confronts Grover and discovers that the supposed ransom cash is actually in the briefcase—but Chip Oswald has seized it in a double cross. Amid the unraveling revelations, Willard learns a startling truth: his father was Crock’s lover and her former manservant. When the police close in on Grover’s hideout, Crock convinces them that the trio are her rescuers.
In the climax, Willard guides the police to Chip’s house, where the ransom money is finally found. Chip pulls a gun, but Rusty, panicked, knocks him unconscious with a lava lamp. Crock expresses her gratitude in practical terms: she pays for Willard to attend college at the University of Southern California and buys him a new Armani suit, while funding Rusty’s plan to open a new Chicken Hole on the beach. Willard reconciles with Hillary, and Crock ends up pursuing a romantic relationship with Grover.
