Maybe it was Y2K anxiety. Maybe something was in the Hollywood water. Whatever the reason, 1999 yielded a bumper crop of movies about angry, ordinary men throwing off society’s shackles and finding something extraordinary in themselves.

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Fight Club and The Matrix purported to see past the blinders keeping everyone in line, and revolted against the sinister forces (capitalism and parasitic brain-vat robots respectively) exerting their invisible control. In American Beauty, a henpecked husband gave himself a new lease on life by rejecting suburbia for a simpler existence of weightlifting, pot-smoking, and skirt-chasing. But the most revealing film of that time, about the stifling influence of work and the evolving mores of masculinity, has to be Office Space.

As profoundly unmotivated systems programmer Peter Gibbons, Ron Livingston and his don’t-give-a-shit shrug provided a generation with a hero. Writer-director Mike Judge has spent his entire career jabbing at the indignities of having a job, and in Peter he found the ideal vessel for his contempt. He punches the clock at the oppressively grey headquarters of Initech, a company whose ill-defined mission might as well be breaking the souls of its employees. It’s the most banal vision of hell: lethal doses of tedium, an unceasingly chirpy customer relations rep one cubicle over, an ineffective flow of management so dense with bureaucracy even Kafka would have banged his head against his desk. Other irritants have more of a personal sting, such as the smug pleasure boss Bill Lumbergh (Gary Cole, doing a bargain-rack Gordon Gekko) takes in by informing his underlings that, yeah, they’re gonna need to come in on Saturday.

Peter and his colleagues’ ill-conceived scheme to get rich skimming fractions of pennies from the corporate kitty gives the loose, shaggy plot a semblance of direction, but Office Space would be more accurately clocked as a character study about a man who refuses to take any more. The aggressive regular-guy-ness of Livingston empowers anyone sharing his middle-income lot – not well-off enough to enjoy being rich; not poor enough to have the hardship to account for his misery – to access him as a surrogate, making his strike against the coffee-slurping overlords into a slacker wish-fulfillment fantasy.

His version of getting unplugged from the matrix comes when a hypnotherapist drops dead in the middle of their session, which leaves Peter in a state of new enlightenment. It means all he must do to change direction is simply decide to do so. He starts coming to work in flannel shirts and jeans, ignoring the memos telling him things he already knows, and eventually skipping out entirely to embrace absenteeism as a philosophy. His willingness to think past the conformity of the zombies pacing the corridors catches the attention of his supervisors and lands him a promotion – perhaps Judge remembered the feeling when he realized the loathing of authority that made him unemployable could mean success in entertainment.

Facebook Twitter Pinterest Jennifer Aniston and Mike Judge in Office Space. Photograph: Allstar/20th Century Fox/Sportsphoto Ltd

While this critic is relieved to confirm that two solid decades of incessant “I believe you have my stapler” stammerings from unfunny men at bars have done nothing to detract from this film’s hilarity, certain aspects have aged.

Early on, during a late-night gripe session with Peter, one of his pals suggests that the stability and consistency of their work may have its merit, and gets summarily dismissed. That Peter and the film itself consider a reliable paycheck a fate worse than death may baffle an 18-year-old today, reared in a world of few jobs for young people, inhumane conditions at the world’s biggest corporations, and millennial burnout. A new generation is leaning in favor of socialism to stop widespread poverty and viciously exploitative business practices. Peter’s idea of suffering is being bored – did we ever have it so good? Take a step back, and a viewer can see people growing more desperate, aware, and politicized in their rebellion.

The other element binding this film to its era are the distinctly male overtones to Peter’s metamorphosis into his best self. He finds happiness by getting back in touch with the physical instincts from which eight hours under fluorescents can estrange a man. He finally ditches his unfaithful girlfriend and shacks up with a local waiter played by Jennifer Aniston, an epitome of cool to Peter for sharing in his apathy. He eventually ends up getting a new gig on a construction crew, which Judge makes out to be good, honest work. At the risk of putting too fine a point on it, Judge even splices in a few shots of Peter catching a fish. The film imagines his transformation not as an evolution, but a devolution in the direction of our primal hunter-gatherer origins.

Though he’s defined by his lack of extraordinary qualities, Peter’s as much of a chosen one as his contemporary Neo. He takes it upon himself to carry the mantle of his fellow men, left flabby and neutered by the creature comforts of mild prosperity. His crusade against the tyranny of the 9-5 would refine its social component to shed the hangups about manliness, and the economic stakes would rise considerably over the following decades. But Peter remains an everyman for his particular moment, an embodiment of the Gen-X ideal, a genuine soul standing tall against sellout-ism – the dream of the 1990s.