It's the year 2000 and things are looking good for Dick Harper (JIM CARREY). Not only does he have a beautiful wife in Jane (TÉA LEONI) and a well-adjusted son in Billy (AARON MICHAEL DROZIN) who's learning Spanish with their housekeeper Blanca (GLORIA GARAYUA), but he's also just been promoted to a vice president of communications spot at Globodyne. A media properties consolidator, the wealthy company is run by the high flying Jack McCallister (ALEC BALDWIN) who wants Dick to do a TV news interview explaining their position.
Unfortunately, and unbeknownst to Dick or anyone else, Jack has embezzled all of the company's money and put the blame on CFO Frank Bascombe (RICHARD JENKINS). With the company bankrupt and its stock now worthless, everyone is laid off, including Dick who had earlier convinced Jane that it would be a good time for her to quit her unfulfilling travel agency job and spend more time with their son.
When neither can find a job and with their finances dwindling, the couple starts selling their belongings, but when their newly sodded lawn is repossessed, that's the final straw for Dick. On a whim, he decides to go out and take what he needs, eventually leading him and then Jane to go on a robbery spree that soon returns them to the lifestyle to which they were previously accustomed. But when they run into Frank and later Jack, they decide to take their criminal enterprise to a higher level by getting revenge on Dick's former boss.