Lester Burnham (KEVIN SPACEY) is a 42-year-old man whose middle class, suburban doldrums far exceed the standard middle-age crisis. His fourteen-year career at a magazine is going nowhere, his perfectionist realtor wife, Carolyn (ANNETTE BENING), drives him crazy and his angst ridden teenager daughter, Jane (THORA BIRCH) barely communicates with him, simply writing him off as "weird."
Things soon begin to change around the Burnham household, however, upon the arrival of several new people who shake things up. While their neighbors on one side are a gay couple, Jim (SCOTT BAKULA) and Jim (SAM ROBARDS), the once vacant house on the other has now been occupied by the Fitts family. Colonel Frank Fitts (CHRIS COOPER) is a stern, military man whose wife, Barbara (ALLISON JANNEY), seems to be in state of domestic shell shock.
Little do they know that their eighteen-year-old son, Ricky (WES BENTLEY), a boy so obsessed with life and beauty that they once institutionalized him for two years, is actually a successful drug dealer with a penchant for videotaping everything, including Jane next door.
While that initially creeps her out, Jane soon starts to find Ricky interesting once she gets to know him. That only disgusts Jane's gorgeous and fellow cheerleader friend, Angela (MENA SUVARI), who thinks Ricky's a pervert although she herself claims she's slept with men just in an attempt to further her aspiring modeling career.
When Lester meets both Angela and Ricky, he finds a stirring within himself that he long thought dormant and perhaps dead. With Angela, who openly flirts with him, Lester goes into hormonal overdrive and constantly fantasizes about her, when not pumping iron to get into shape and make himself more attractive to her.
With Ricky, Lester finds a kindred spirit whose carefree attitude about life and work -- as well as the expensive pot he sells him -- causes Lester to change his outlook on life. Having successfully blackmailed his former company, Lester sets out to have a good time, not caring that his wife may be seeing local real estate king, Buddy Kane (PETER GALLAGHER).
As everyone reacts to Lester's newfound attitude with shock, he must deal with the fact that Carolyn doesn't like his new self, that Jane half-jokingly asked Ricky to kill him, and that Colonel Fitts becomes suspicious of Lester's involvement with his son.