In many ways, Office Space may genuinely be twenty years old but in many, many other ways, the film remains a timeless satire of the corporate workplace environment today as it did when if first was released in theatres back in February of 1999. While not initially successful, the film gained a second life on home video and cable, growing into one of the biggest cult films, beloved and frequently quoted.
Peter Gibbons (played by Ron Livingston) works at a software company called Initech along with his friends Samir (played by Ajay Naidu) and Michael Bolton (played by David Herman), the latter of whom hates his name because he shares it with the singer of the same name. Peter is struggling at work and has grown to hate working at Initech, but continues to trudge in every day, even if he has to take his first break an hour later (to be fair, he sits next to a woman who answers the phone, chirping repeatedly, "Corporate Accounts Payable, Nina speaking. Just a moment. Corporate Accounts Payable..." The bane of his existance is his eight different bosses, in particular Bill Lumbergh (played by Gary Cole), who is obnoxiously condescending. One night, his girlfriend takes him to see an occupational hypnotherapist to help with his depression about work. However, the hypnotherapist dies before he can finish his therapy with Peter. As a side effect, Peter stops caring about work and blows off going in to work overtime that weekend. He also blows off work during the week to spend time with a waitress he likes at a local restaurant, Joanna (played by Jennifer Aniston), who has her own troubles at her job. At the same time, the company has brought in two efficiency experts to try and improve things around the office, both named Bob (played by John C McGinley and Paul Wilson). It is their arrival that causes worry for a number of Peter's co-workers, including Tom Symkowski (played by Richard Riehle) and office oddball Milton (played by Stephen Root).
The film was written and directed by Mike Judge, drawing from his own time as a software engineer until his animation career took off (he is responsible for shows such as Beavis and Butthead and King of the Hill). It is that real life experience that makes so much of this film ring true for so many people. From the mundane everyday tasks to the little annoyances in the office that can drive a person crazy, such as annoying co-workers, or in the case of Samir the fact that no one can or cares enough to learn how to pronounce his last name correctly. The battles with technology also ring true, especially with one continually malfunctioning printer that leads to the best scene in the film of the three main leads destroying it with a baseball bat in a spot on spoof of a gangster movie beat down scene out of something like Goodfellas or Casino and became something that would be spoofed itself several times over the years, most memorably in Family Guy. With Joanna's character, the film also delves into the soulessness of working for a chain restaurant (or any sort of chain store company) and having to strictly adhere to certain guidelines, as evidenced in her boss' obsession with the number of pieces of flair (decorative buttons) she wears on her uniform. It is even more hilarious that all of this mundane corporate satire is played out to a soundtrack that is almost exclusively gangster rap, which adds a certain level of absurdity to the proceedings.
The cast for the film is top notch with Ron Livingston making for the perfect everyman character. Anyone who has worked in an office environment can probably have related to his struggles at one point or another, especially anyone who has hated their job but yet not been brave enough to quit. In fact, many who were in that situation have found inspiration in Peter's story arc to do just that. Michael and Samir are just as sympathetic in roles, brought wonderfully to life by David Herman and Ajay Naidu. Jennifer Aniston does well as Joanna, bringing out some of the workplace frustrations of working in the service industry that nicely compliments the ones depicted for a corporate workplace. Gary Cole plays Bill Lumbergh perfectly, capturing every bad, micromanaging boss ever in one unnervingly even keeled performance. Just a drawn out "Yeah..." is enough to bring him instantly to mind. Stephen Root as the socially inept Milton has perhaps become as iconic as the film itself, which was actually based on a series of shorts based on the Milton character. Root makes Milton such an unique character, shuffling around the office, mumbling all his lines and obsessed with his red Swingline stapler. It's a marvelous comedic performance and Stephen Root just steals every scene he's in.
Office Space is a movie I feel will continue to live on as a beloved cult film for many years to come. Many aspects of the film feel as fresh and funny as they did in 1999. Some aspects are hilariously out of date (for example a 3.5" floppy disk figures into the plot in the second half of the film). But in a larger sense the film still holds up just as much as it ever did. It's a film I loved when it first came out and love even more now that I work in a corporate office myself. I still remember when I first had a problem with an office printer and remarked, "Oh man, this is just like Office Space!" Like I said, infinitely relatable.