In January 2000, Dick Harper (Jim Carrey) receives a promotion to Vice President of Communication at Globodyne. Almost immediately, he finds himself on the show Money Life, where host Sam Samuels and independent presidential candidate Ralph Nader label him and the company's workforce as "perverters of the American dream," accusing Globodyne of making the rich even wealthier. As these allegations unfold, the company's stock begins to plummet, leading to the swift devaluation of the employees' pensions tied to Globodyne shares.
Returning home, Dick is greeted by his exuberant wife Jane (Téa Leoni), who shares her decision to resign from her job to focus on their son Billy. However, during dinner, Dick must break the devastating news about the company's downfall, leaving Jane visibly shaken. With a hopeful outlook, Dick attempts to secure a Vice Presidency at various firms over the following months, but each effort is met with rejection. To exacerbate their troubles, Jane reveals the impending doom of their finances, as their assets consist entirely of now-worthless Globodyne stock, pushing them towards bankruptcy.
Faced with the reality of their financial struggles, both Dick and Jane begin applying for low-wage jobs but face further setbacks with each endeavor. As eviction looms just 24 hours away, they make a drastic choice—turning to a life of crime. Dick's first attempt involves his son Billy's squirt gun in a robbery at a local convenience store, but he backs out, settling for a slushy instead. After a series of failed attempts, they finally manage to rob a head shop, discovering an unexpected thrill in their criminal acts.
Emboldened by their initial success, they plunge deeper into a routine of theft, becoming increasingly adept at their nighttime escapades. This new lifestyle allows them to accumulate enough money to retrieve their car and home, both of which were on the brink of repossession. Their most ambitious heist becomes a bank robbery, where they plan to masquerade as corporate security. However, chaos ensues when another couple, Oz and Debbie Peterson (Carlos Jacott and Stephanie Weir), attempt a botched armed robbery, getting caught almost instantly, while Dick and Jane narrowly escape without any loot.
The Harpers decide to retire from crime after witnessing the Petersons’ unfortunate fate. However, Dick is soon haunted by the news that he is at risk of indictment due to his unintentional involvement in Globodyne's downfall. Finding solace at a local bar, he encounters Frank Bascombe (Richard Jenkins), the former CFO of Globodyne, who unveils the truth about the company’s corrupt CEO, Jack McCallister (Alec Baldwin). Bascombe discloses that McCallister absconded with the company's assets and profited handsomely, leaving the rest in financial ruin.
Determined to seek justice, Dick and Jane plot their revenge with Frank’s help, learning McCallister is about to transfer $400 million in bearer bonds to an offshore account. The couple devises a scheme to intercept this transfer and substitute it with a forgery. Unfortunately, the plan unravels, leading Dick into a confrontation with McCallister, where he utters a bitter ultimatum. Undeterred, Dick reveals to Jane that he intended for McCallister to sign a blank check, enabling Jane—an art major in college—to forge it.
The following day, as McCallister departs his mansion, he is quickly surrounded by reporters and former Globodyne employees clamoring for attention. Dick seizes this moment, presenting McCallister with a prepared statement that leads the disgraced CEO to announce, amidst disbelief, that he allocated $400 million to support the failing pension plan for Globodyne’s former employees. As the crowd erupts in cheers alongside Dick and Jane, the revelation of McCallister’s fraud becomes evident.
In a heartwarming conclusion, the duo is seen delivering checks for pension funds, including to the now-jailed Oz and Debbie, while the fallout leaves McCallister with just over $2,000 to his name. The film closes with the Harper family—now wealthy once again—driving into the sunset in a Volkswagen. Enthusiastically, Billy attempts to teach his parents some Spanish, just as a Bentley pulls up, revealing Dick's friend Garth, who offers Dick an exciting new job opportunity at a company named Enron.
