The Twisted Comedic Genius of the Movie “Office Space”
And what it can teach us about writing characters
On Sunday, I went to a movie night with some friends, and I was tickled to see they’d chosen Office Space, the Mike Judge cult classic comedy from 1999.
Office Space was probably the first comedy—that I know of, anyway—to totally nail office tech culture. I hadn’t re-watched it in over a decade though, maybe longer, and I was curious how it would hold up. Movies that dissect a bygone decade can feel old—especially when it comes to comedies.
But, happily, this was not the case. Not only did Office Space hold up, it was even funnier than I remembered. The script is tight and hilarious. There’s not a wasted scene or a wasted word. The pacing is perfect, and every scene feels like it propels the story forward and adds something essential and weird to the universe.
Most impressively, re-watching reminded me just how pitch-perfect the characters are. First-rate casting and acting take Office Space from a good comedy to a timeless classic. In a solid comedy, maybe you have one or two memorable, quotable characters. In Office Space, it’s like ten highly memorable, quotable characters—basically the entire ensemble cast.
I thought it would be interesting to look at Office Space from that angle: the characters, and why they work so well.
Now, part of the answer is that Mike Judge had great instincts for which character actors would work here, and he nailed the casting. But I think it’s more than that. There’s something about the Office Space script, and the comedic universe it builds that’s quite interesting to me as a writer.
What is that?
Years ago, I took a comedy workshop from the actress and comedian Jill Bernard, and basically it was about finding comedy through conflict. And one part of the workshop was Bernard explaining that conflict is not limited to people fighting each other. She outlined at least three kinds of conflicts:
Man vs. Man: the obvious one. People with opposing interests or personalities tangle with each other.
Man vs. Himself: Someone suffers from a fundamental delusion, fear, or character flaw, and this person is their own undoing.
Man vs. Nature: It’s the universe itself that has it out for our character. Nature here really means “whatever world we’re in.” It’s not restricted to just Mother Nature but rather the whole of reality apart from the characters themselves.
Each of these conflicts adds a new flavor of comedy. In Office Space, we get all three, and they’re all dialed up to 10.
You could say that Office Space asks this question: “What is this character’s deepest fear? What is their fundamental insecurity?”
It then gives the character exactly what they most fear. And it does this not just for the protagonist but for basically everyone. The characters in Office Space are made to either undergo an ultimate torment, or to be an an ultimate tormentor, or both.
Peter Gibbons
The humble protagonist, Peter is a burnt-out software engineer stuck in a dull job. His core desire is peace and freedom. He wants to just chill out and be left alone. His greatest fear is being controlled and forced to waste his life on meaningless drudgery.
Sadly for Peter, his whole world is designed to make his fears come true.
He drives to work in congested rush hour traffic, sitting a in lane that won’t move. The other lane buzzes along, so he switches lanes, and as soon as he does, that lane grinds to a halt. Then he does it again, and the same things happens. The rule is: The lane that’s moving is whichever one Peter isn’t in. An old man on a walker on the sidewalk passes him.
Every time he enters the office, the front door gives him a static electric shock.
He works in a windowless cubicle, surrounded by co-workers who grate on his psyche. Nina across the cube answers phone calls repeatedly, in a cloying voice, “Corporate accounts payable, Nina speaking, please hold.” Her voice is so repetitive and annoying Peter literally has nightmares about it.
Milton, his weird cube neighbor, listens to the radio without headphones, at a distracting volume, and refuses to turn it down, even when Peter asks nicely.
Aside from his sympathetic pals, his fellow engineers Samir and Michael, the rest of The Office is equally annoying, rubbing their chipper or dysfunctional personalities in Peter’s face.
His Boss Lumbergh harasses him about absurd minutiae—like putting the cover on TPS reports. Lumbergh then re-sends him memos that Peter has already read. Peter’s other bosses—we learn he has eight bosses total—stop by to have the exact same demeaning conversation with Peter that he just had with Lumbergh.
Peter is trapped in a Sisyphean hell of TPS reports.
To make matters worse, when Peter has weekend plans—his only real shot for freedom— Lumbergh asks Peter to come in and work full days on Saturday and Sunday.
Even his girlfriend Anne, who all his friends agree is probably cheating on him, insists that Peter himself is the real problem and that he should skip his guy’s poker night and go to a freaky hypnotherapist.
Peter’s totally boxed in, and, at the beginning of the movie, he doesn’t have the wherewithal to break free. Of course, he eventually does break free, and this is part of his character arc. But before this happens, we’re treated to a world designed to subject Peter to maximum annoyance and mind-numbing repetition of tasks and rituals that don’t matter.
Samir Nagheenanajar and Michael Bolton
Michael and Samir are Peter’s best friends in the office. They’re both relatively smart junior software engineers who don’t get much recognition or respect.
They’re competent men trapped in a sea of incompetence. But, like Peter, neither of them has the will to escape. So they just bitch and moan together.
Michael Bolton is further humiliated by sharing a name with a famously uncool singer. He wishes people in the office would stop bringing it up, and he even suggests that maybe he’ll start going by “Mike.” But everyone keeps bringing it up, one of the Bobs—the redundancy consultants in the movie—even suggesting, “You must love him [Michael Bolton the singer] twice as much because you share his name!”
Samir gets his own form of disrespect-via-name, and it’s one of the movie’s many running gags that no one can pronounce his name. This is exploited perfectly when one of the Bobs harnesses a bit of silly Xenophobia:
Bob: “Samir… Naga… Naga… not gonna work here anymore, anyway.”
(apparently this line was improvised)
And both Michael and Samir are subjected daily to a fax machine that doesn’t work and gives them stupid error messages, as when Michael screams, “PC Load Letter? The fuck does that mean!?” (It means it’s out of paper.)
Michael and Samir ultimately suffer the final indignity: they get laid off for no reason, even though they’re both good programmers, while Peter gets rewarded by the Bobs for being more confident. The Bobs don’t care about good programmers, they just want to be entertained by a guy who stands up to them and has charisma.
Tom Smykowski
A long-time employee with a dubious job (“I take the specs from the customers and bring them to the engineers”), his fundamental trait is job insecurity. His fear is irrelevance and being exposed as useless. Deep down, he knows he doesn’t actually do anything valuable—he’s just a middleman, he explains to the Bobs, and he’s needed at Initech because engineers don’t know how to talk to customers.
His personal hell is being asked by the Bobs, point blank, “What would you say… you do here?” His nightmare isn’t not merely being laid off—it’s being seen, judged, and found lacking. In one of the best rants in the movie, Tom tells the Bobs:
Tom: “Look, I already told you! I deal with the goddamn customers so the engineers don't have to! I have people skills! I am good at dealing with people! Can't you understand that? What the hell is wrong with you people?!”
Of course, he gets immediately laid off (“This guy is useless. Doesn’t do anything,” the Bobs tell Lumbergh). Then Tom goes on a downward spiral, tries to kill himself… and fails. Then fate “rewards” him with a huge injury settlement after he’s hit by a truck. Now Tom is finally rich and happy because he no longer needs to justify his existence. His body is broken, and he’s in immense pain, rolling around in a wheelchair like a human piñata, but, hey, at least he’s free.
Tom’s story is pure comic reversal: He only gets peace when the system removes him entirely and rewards him in an arbitrary way.
Milton
Truly Office Space’s weirdest character, Milton’s fundamental character trait is being a weakling that everyone steps on, especially his bosses. His biggest fear is being pushed around and disrespected, especially by having his desk moved and his stapler stolen.
So, of course, Lumbergh eventually steals Milton’s favorite red stapler, uses his office as a storage closet for random boxes, then moves Milton down to the basement and tells him to exterminate the roaches.
In one of the movie’s most surreal scenes, Milton is sitting in a dark, dank basement, with Lumbergh sipping his coffee and telling Milton to find the roach spray and get to work. It’s a bizarre scene and a perfect escalation.
But the humiliation is not complete. As The Bobs reveal, Milton was actually laid off five years ago, and no one bothered to tell him. But due to an HR glitch, he kept getting paid. Rather than tell Milton what happened, in a final act of disrespect, they simply stop paying him.
The comic reversal for Milton is that he takes his revenge by burning the entire building down—and, in the process, finding the $300,000 in travelers checks that Peter tried to return to Lumbergh. But because no one gives a shit about Milton, no one notices or suspects him of the causing the fire, and he escapes to a resort in Mexico.
Joanna
Joanna appears as a kind of foil to Peter’s character arc and his emotional need for freedom. Peter has a crush on her but feels constrained by the arbitrary rule that “you can’t ask your waitress on a date.” Why not? Well, you just can’t.
Once he gets hypnotized and breaks free of social expectations, he asks her out with total confidence and zero worry about whether they’ll end up together. Naturally, this is highly attractive and they end up as boyfriend-girlfriend.
But true to Office Space’s world-building, Joanna is yet another victim of a soul-crushing system, albeit in the flavor of an chain restaurant that forces employees into performative enthusiasm with pieces of “flair”—just random, stupid buttons—on their uniform.
So, even Joanna—who is clearly the most, grounded reasonable character in the movie—also lives in her own form of hell.
Her desire is to be left alone to do her job with a clear set of expectations—and not be judged for an arbitrary, meaningless “flair”rule. And her personal hell is her passive-aggressive manager, Stan, who harps on her “lack of flair” without ever explicitly telling her what the expectation is.
Joanna fights a soft power version of control: she’s told that she has “freedom” to express herself—to choose how many flair buttons she wears—but she’s punished for not conforming to unspoken, nonsensical rules about “doing more than the bare minimum.”
She finally flips out when Stan tries to guilt-trip her yet again:
Joanna: “So if you want me to wear thirty-seven pieces of flair, why don't you just make the minimum thirty-seven pieces of flair?”
That line is almost a thesis statement for Office Space: If the system has arbitrary, insane standards, just say so—don’t pretend we’re free, and don’t pretend the system treats us equally.
Bill Lumbergh
Peter’s obnoxious boss, Lumbergh is the the personification of The System. He parks his Porsche in a reserved spot, and his job seems to mainly consist of walking around the office sipping coffee and harassing his employees with minutia. His dialogue, and his delivery, is that of a maximally annoying, passive-aggressive bully.
Lumbergh embodies the toxic work culture and give it an absurd face.
But although he is absurd, he is human. He too has desires and pain. Lumbergh’s core desire is to boss people around and subject them to the whims of The Initech System. His character arc is the precise opposite of Peter’s: As Peter breaks out of hell, Lumbergh descends.
When Lumbergh finds he can no longer control Peter, all of his passive-aggressive power moves crumble. Lumbergh tries to bully Peter, and Peter just physically walks around him and doesn’t take his calls. When Lumbergh tries to fire Peter, The Bobs push back and promote Peter instead. Then Peter takes Lumbergh’s parking spot, and a tow truck wrecks Lumbergh’s Porsche, pulling the bumper clean off.
In this cinematic world, Bill and Peter cannot both be happy. One of them has to be miserable.
A character’s deepest fear
In satire and comedy, a powerful way to expose an absurdity is to use that absurdity to turn your characters’ lives into a living hell.
As a writer, you can ask these questions:
What is my character’s deepest fear, insecurity, or delusion?
How can everyone else around them exploit this fear or make this fear come true?
How can the other characters exploit or expose my character's insecurities or delusions?
And how can the world at large—the world this character inhabits—reveal my character’s fears and insecurities and twist the knife into their psyche?
This is what Office Space does with majesty, not just to the protagonist but to an entire ensemble.
This ethos of torment makes these characters not just funny but 100% philosophically consistent with the idea that the system exists to terrorize each person in the way they find personally most insulting.
And ironically, this is how Office Space shows, lovingly, that every character matters.
Now do Idiocracy. Every character in that is dialed to 11.
Wow great insights! Thank you for writing this.