The first time Mike Judge worked in an office, he lasted three weeks.

While taking time off from college, he landed a job alphabetizing purchase orders through a temp agency. The idea of sitting in an office intrigued him, until he learned the reality of his mind-numbing responsibility. “You’re just alphabetizing all day long,” Judge says. “I’d be home and I’d be alphabetizing in my sleep. This was like water torture.”

After graduating, Judge found more meaningful work as an engineer for a military contractor on Coronado Island, processing schematics for F-18 fighter jets. One day, he stopped by a colleague’s desk to say hello and stumbled into what would eventually become his first animated character. “He just went into this whole thing about how he was going to quit because they moved his desk again,” Judge remembers. “I said, ‘Well, why don’t you want the desk to move?’ It was something about his fish tank: ‘I told Bill, they move it one more time, I’m outta here.’ I remember thinking, they could move your desk 20 more times; you’re not going to quit. He just enjoyed complaining.”

Not long after, in 1991, once Judge committed to pursuing his childhood animation dreams, he took the “bits and pieces of those places” and, using a recently purchased Bolex camera, constructed a short film called Milton’s Office Space. The cartoon, which Judge drew and voiced, centered on an agitated, whining employee and his smarmy, passive-aggressive boss. Comedy Central, a brand-new network at the time, paid him $2,000 for it, beginning Judge’s blistering trajectory as a prolific comedy mind.

The pencil drawing and cubicle experiences eventually inspired Judge’s live-action directorial debut, Office Space. Released 20 years ago this week, the comedy, at first a box office flop, took on cult classic status by holding up a mirror to the depressing, cynical, and occasionally farcical nature of the modern office. The premise, about a software company employee who stops caring about his soul-sucking job, provided catharsis for many who also felt trapped by micromanaging bosses and offered an antidote to their 9-to-5 monotony.

“That’s what we all loved about it—it was a totally authentic view about the horrors of working at an office,” says Daniel Rappaport, one of the movie’s producers.

But turning Judge’s semiautobiographical and hyperspecific vision into a collaborative medium didn’t come without its challenges, battles, and mistakes. Below is the story of how one of the best creators of his generation produced an endlessly relevant world of annoying colleagues, lurking bosses, broken printers, red staplers, “flair,” and the desire to burn it all down.

Part I: “I Think We Have a Real Movie Here.”

Judge’s first animated series, Beavis and Butt-Head, premiered in 1993 on MTV. A ratings hit with an edge, the show made Judge a hot item in Hollywood. Studios came calling with one question: Got any ideas for a movie?

Daniel Rappaport (producer): Beavis and Butt-Head had exploded. Everybody wanted to be in business with him.

Mike Judge (writer, director): The Aspen Comedy Festival played a bunch of my stuff, including my original animated shorts. That’s where [Fox Network president] Peter Chernin saw the Milton short—at that point, I had done three more for Saturday Night Live—and said, “This should be a movie.” I think he was thinking of a Walter Mitty–type thing. I was in the process of writing the King of the Hill pilot and doing the drawings and then they said, “Let’s get some writers to come in and pitch.” I didn’t see a whole movie in Milton; I wasn’t sure how to do that. To me, he was somebody that I kind of didn’t want to know what he does when he goes home.

Sanford Panitch (executive vice president at 20th Century Fox, current president of Columbia Pictures): We all recognized there was something special in Mike’s voice. Honestly, you just laughed out loud when you talked to him about his ideas and about where his inspiration came from.

Rappaport: There was no issue with any studio betting on Mike at that point. He could go in and pretty much pitch anything to anyone and we’d probably sell it.

Judge: Fox said, “What if it was a workplace comedy, like Car Wash and it’s an ensemble?” I had been wanting to do something about engineers since I started. Once they said that, then I said, “I can do this myself and I’ll try writing this.” I wrote up a treatment really early in 1996, turned it in to Fox, they really liked it a lot, and then I started one of the busiest years of my life where I was doing the Beavis and Butt-Head movie, then King of the Hill. I started writing the screenplay the summer of 1997.

Panitch: The script was really rough. For me, the awakening was when I would fly down to Austin where Mike lived and we would just sit around with his instruments—he’s actually a talented musician—and he would just tell me more of the stuff that would happen in workplace environments.

David Herman (Michael Bolton): Mike and I and Stephen Root had all worked together on King of the Hill. The person who was casting the pilot for King of the Hill had also done MADtv, so they knew I was able to do diverse stuff.

Stephen Root (Milton): [Judge] had told us he was writing [a script]. But the first time we really heard about it was when he wanted to do the table read for Fox. He said, “We’ll all go over in a group and read it to them.”

Judge: That would have been in September of 1997. We had a bunch of actors come in just to sort of see how it reads as a movie. The only ones who were actually in the movie were Stephen and David.

Root: It was a fairly big meeting for him. Not for us. We had a job we were happy with, but we were happy to go help him.

Judge: I was going to read the voice of Milton, because I had done the voice in the cartoon. Stephen was going to do a bunch of other little parts like the hypnotist, because him and David on King of the Hill had both done a hundred characters. They’re both incredible. At the last minute I started to get cold feet about reading Milton. I wanted to just sit back and listen and not be a part of it, and I just had this epiphany: “Stephen Root, of course”; that’s who should do it.

Root: I went, “Thanks for the prep.”

Judge: He was sitting there looking at the tape, concentrating, and I could kind of hear him start to do it, and I said, “Yes this is great, can you do it?” He just killed it at the table read.

Root: I wanted to grab it more and give it more of a lisp because that’s what I felt it needed. We had no illusions of doing the movie. I actually had a fantastic time doing the psychiatrist. I had the entire room believing I was dying of a heart attack. I think that was my best performance of the day.

Judge: I did imagine David Herman playing Michael Bolton the whole time I was writing it.

Herman: I think what he had seen me play on King of the Hill was a weenie desperately trying to be a man. I think Michael Bolton, what I attached to at his core, is he really is this quashed peon who is trying to maintain his manhood, living in this quiet desperation, trying to still be like, “No, I’m tough, I’m a rapper, I’m a marine.”

Judge: Dave was great. Other people were all right. But I thought it went horribly. The guy who read the lead didn’t quite get it, really. He wasn’t doing it the way I saw it in my head at all. After that read, I just thought, “This isn’t going to work at all—I guess we’re not making this movie.” But then [Fox Film Group president] Tom Rothman was surprisingly positive. [He] was like, “No, the actors weren’t right, but I think we have a real movie here.” I kind of thought, “Well, if you say so.” [Tom Rothman declined to be interviewed.]

Root: I was like, “Well shit, now I’d like to do it.” Mike liked me for it. I had to go through the machinations and go through an audition. He said, “I want you for this, but you’re not a name and it’s a fairly important part.” That’s fine, I do that every day.

Judge: The studio made Stephen come back and read three times. They really wanted to try and get some big star in that role, so I just waited them out.

Part II: “Sometimes, It’s the Rope-a-Dope.”

With Root and Herman on board, the studio set out to cast its protagonist, Peter, and the ancillary characters. In accordance with Judge’s vision, the supporting players were then mostly unknowns—which prompted a few debates with the studio.

Rappaport: Studios inherently want to cast some name brand in the lead of a movie.

Nancy Klopper (casting director): From the very beginning, it was off to the races. I started reading actors and Fox said, “How about Matt Damon or Ben Affleck?” Good Will Hunting had just come out, so they couldn’t have been any hotter. We went to them with the script and Mike ended up having a meeting with Matt Damon in New York, but ultimately Matt decided it just wasn’t going to be for him. [Matt Damon and Ben Affleck did not respond to an interview request.]

Judge: [Damon] was a real nice guy and said he thought the movie could be good. Daniel Rappaport told me, “He wants to do it.” I don’t think that was the case. It was an 11 a.m. pizzeria meeting. I’m sure he would have been great, or Ben Affleck, but it didn’t need to be a strapping, tall leading-man type.

Rappaport: Mike was looking for something specific and had narrowed it down to this idea that he was looking for a young Jack Lemmon from The Apartment.

Ron Livingston (Peter Gibbons): I was at a place in my career where I just auditioned for all kinds of things. I had two or three auditions a week for stuff most likely I wasn’t going to get. You’re just putting yourself out there trying to get a bite.

Klopper: While that was happening, Ron Livingston came in to read for me.

Livingston: I really liked the scenes. I thought there’s something fresh about it.

Usually when you go to an audition, you’re either standing or sitting in a chair in front of a camera. I couldn’t figure out how to play that [TPS report] scene standing or sitting in a chair. In the far corner of the room, Nancy had her desk with a phone and drawers and files, and I just kind of walked over and said, “Can I do the scene here?” She said, “Oh sure,” and turned the camera around, and it kind of came to life a little bit. I was temping at the time, so I felt comfortable sitting at a desk, answering a phone, and futzing with the drawers.

Klopper: I was like, “Oh my god.” His reading was so fantastic, his understanding of Mike and the way Mike writes and the cadence in which the characters speak—I thought he really nailed it. I videotaped him and I called Mike, and I said, “I’m going to send you something you’re not going to believe.”

Judge: There was something funny to it without looking like he was trying to be funny. He had the perfect cadence that I was looking for that I hadn’t found anywhere else. I know he wasn’t a bankable star, but originally, the idea was this was going to be a little movie.

Rappaport: He was perfectly human, funny, and relatable. Mike was like, “That’s my guy.”

Judge: What most actors did was played it like “This place is bullshit and I deserve better and I’m going to get out of here.” To me, the attitude was, “I’m actually lucky to have this job.” It makes the fact that I don’t like it more depressing because I didn’t think I deserved better. Ron played it like that.

Livingston: [I got] a really funny call from my reps. I thought it was just going to be the big pep talk—“Good luck with the screen test”—and then they said, “The studio wondered if you could fast until then.” This was on a Friday, the screen test was on a Tuesday. I laughed because I assumed they were kidding—it turns out they weren’t. I was like, “All right, I guess that’s what I got to try and do.” I didn’t get very far.

Tim Suhrstedt (cinematographer): When I first came on, Mike knew he wanted Ron and [the studio] was still pushing Ben Affleck. I have to stress how respectful he is. He was like, “I think Ron’s really the guy and I don’t think this is a movie about movie stars.” We did some screen tests while they were waiting to negotiate with Affleck. We brought Steve Zahn in and Noah Wyle, and they tested Ron again. I know Mike was frustrated because he doesn’t like to disappoint people. He didn’t want to bring in an actor [when] he knew he didn’t want them, but he had to do it for the studio.

Livingston: You weren’t really privy to the conversation about who else was in the running and who else was going to get it. You bought a lottery ticket and you were waiting for them to read the numbers off.

Suhrstedt: One day after screen tests, they were like, “Ben Affleck wants $2 million and we’re not going to pay that.” Mike thought that was hilarious, like “Why didn’t you figure that out before you jerked me around?”

Judge: There was a lot of that—going out to big stars and coming back to me and saying, “Sorry, [we] can’t pay that kind of money.” Well, I didn’t ask you to go out to him.

Panitch: At the end of the day, you’re making a wide-release movie. It’s a natural instinct to go after someone with known talent like that.

Klopper: They said, “Well then, you’re going to have to go with a name for the waitress Joanna.” So that’s how the Jennifer Aniston of it all happened.

Rappaport: Sometimes, it’s the rope-a-dope. It’s not unique to this movie, it’s the Hollywood process. At a certain budget level, they can’t get a big star because they can’t afford it. Jennifer had made a couple big movies; she was a giant star off Friends, and that made the studio more comfortable. At the time, we also represented Jennifer, but she wanted to do the movie. [Through a representative, Jennifer Aniston declined to be interviewed.]

Klopper: She just wanted to work with Mike. That’s really how that happened. She’s very funny and a fabulous comedic actress. That was the trade-off.

John C. McGinley (Bob Slydell): Mike sent everybody cartoon illustrations of Lumbergh, and so you went into auditions and everybody auditioned for Lumbergh. They called back and said, “You want to be one of the Bobs?” They’re hardly on the page and I said, “Well, yeah it’s a really funny script.” I thought [Mike] was great, I’d seen him on the surf in Malibu a bunch of times and I was like, “Yeah, I want to do it.”

Gary Cole (Bill Lumbergh): All I did was rip off the cartoon. It was so perfect anyway.

Rappaport: Gary definitely used that as inspiration. [But] he’s a brilliant comedian, so he brought his own unique flair.

Cole: As I watched it I remembered a couple of asshole bosses I had and that’s the other thing that made me chuckle. Not only that it was funny, but it was funny because it was real. So I just basically tried to impersonate it.

Judge: He was doing a spot-on impersonation, but he brought it to another level. It was a lot funnier than what I was doing. He had this sort of darkness to him I loved.

Ajay Naidu (Samir Nagheenanajar): I was living in California doing a series at the time. My agent attached a note saying everybody loves this, everybody wants to be in this. I thought the character, as opposed to being Indian, should be Middle Eastern, and I gave that accent a whirl in the initial audition.

Klopper: I’m sure I read every Indian actor who had a SAG card on both coasts. … We put him on tape in New York. I saw it and went, “Wow.”

Judge: I had the character as being Iranian because my good friend at my first engineering job was Iranian. I wanted to have a Middle Eastern character where the jokes aren’t just all about that. We ended up settling on Jordan. I wanted to go with something he felt comfortable with and boy, he just went and studied the accent and did it really well.

Diedrich Bader (Lawrence): I had just seen Bottle Rocket at the New Beverly. I really thought Owen Wilson was cool, so I worked up this character that was just like Owen Wilson. I signed in for my audition and sat down, and Owen Wilson walked out of the room. I couldn’t do a better impression of Owen Wilson than Owen Wilson, so I came up with the Lawrence character on the walk into the room with three or four seconds of adjustment time. [Through a representative, Owen Wilson declined to be interviewed.]

Klopper: I was very excited about the fact that [Wilson] and Vince Vaughn both came in. Owen was a real sweetheart and I thought his reading was really hilarious. Vince took a lot of scheduling and rescheduling and cancelled appointments to get him in, but he finally came in. I think a lot of Diedrich was just his physicality. It was pretty instantaneous that [Mike] wanted Diedrich.

Bader: The last I heard was they had gone out to Billy Bob Thornton and that he was considering it, but I think he wanted $5 million. I think that the whole production was $5 million. So it finally came to me. [Vince Vaughn and Billy Bob Thornton did not respond to an interview request.]

Klopper: I have to confess that I was kind of campaigning for Owen. I thought Owen was really funny and he was on the way up, and I thought that it would be satisfying to the studio and that maybe it would take a little pressure off us wanting to use Ron Livingston.

Bader: We rehearsed with Ron in Mike’s trailer. I remember we had gone out to dinner the night before. We went to a Tex-Mex place and Ron had ordered these deep-fried things where they wrap a tortilla around meat and deep-fry it and that’s all he ordered, like three of those. I was like, “Dude, what’s going on with that?” And he goes, “The studio wants me to lose some weight.” I found it really hilarious—all the things on the menu, deep fried meat is probably the worst choice he could’ve made.

Livingston: It’s probably true. I don’t think I was trying that hard. I think I was making a slight attempt.

Part III: “I Felt Like We Were Almost Making a Documentary.”

Office Space depends on its bland, bare environments, which put the suffocating monotony of work and life into greater relief.

Panitch: Mike didn’t really believe in production design. I remember them sending me a picture of the office, and it was literally like an office that you’d rent from those office rentals. We were very concerned it was going to look so boring on film.

Suhrstedt: Mike was always very clear that he wanted it to look realistic. He wanted the place to be sort of “gray on gray” and feel almost surreally boring. We had a lot of time to shot list, and I think he got more confident as we talked about the material. We literally tested different shades of gray.

Carla Curry (set decorator): We created that whole thing in an empty building. I had to find a company that would make cubicle walls for us that would all match and be the right height and work in the configuration that they needed them to be set up in.

Judge: They went and ordered these cubicles and they were low, you could look right over them. That’s not going to work for when [Peter] wants to sneak out or when he wants to talk to Milton.

Suhrstedt: The standard cubicle size is 4 feet. Mike wanted 6-foot ones because he wanted Lumbergh peering over the top. He wanted people walled off.

Richard Riehle (Tom Smykowski): [Mike] had a visual sense of what he was trying to get with all of that. He had lived that world. He had really understood that stuff. He would talk about “prairie dogging.” And you go “What?” And he says, “ You know, when people stick their head up.”

Judge: What we ended up doing was they just bought three cubicles of the tall ones and the rest were propped up on apple boxes. Depending on the camera angle, we would just move the big ones wherever they needed to be.

Livingston: [The office] actually looked a little different when you walked in a couple days before shooting. It was just more decorated and there were plants, and everybody had their own individual stamp, kind of the way an office would look in When Harry Met Sally. Mike just walked around with a trash can just saying, “No, lose this, get rid of this, this wouldn’t be here, take all of this off the walls,” and stripped it down to that really bare, kind of soulless, impersonal environment. I think that’s what those places really looked like—nobody lives their lives in there.

Naidu: He’s very astute when it comes to what people are going to see, what they’re going to feel. How objects and environment make people feel. I’ve hated fluorescent lights since I was a little kid. It’s one of the things I hated about school. Mike was really in tune with all those feelings. Making someone feel shitty is the idea of addition by subtraction. You just take more away and all of a sudden, it’s like, “Where are we?”

Herman: It was exactly what I thought his vision was. He really wanted to put a mirror up to exactly what that world is, those passive-aggressive workspaces.

Panitch: Literally, sometimes I felt like we were almost making a documentary.

Melinda Eshelman (costume designer): We made these bad company T-shirts so those would end up going on random people in the background, and Mike was very much into “666” and “Corporations are Satan.” If you look, Initech is based on a six-sided thing. The custodial guy was from “Yale Janitorial Services.” I have one of those badges still. Peter lives in the “Morningwood” apartments. There were a lot of side jokes in there.

Judge: I don’t like getting self-referential at all, but that one was funny. We couldn’t use the real name of the place and I’m glad a couple people noticed.

Rappaport: There was some [studio] concern about how bland Peter’s apartment was.

Bader: It looked like an actual bachelor pad because it was just so shitty, like anonymously shitty. That’s most guys’ apartments. They just want a bed and a TV and a place to sit down. That’s when I knew I was in good hands.

Rappaport: You watch an episode of Friends, there’s no way they live in that apartment in New York City. Mike went out of his way to make it feel authentic to this Ikea apartment this guy would have out of college in a job that he wasn’t enthusiastic about, so he didn’t put anything on the walls.

Herman: You wouldn’t get your deposit back if you put posters on the wall.

Curry: We wanted it to be extremely barren and depressing. He didn’t even have an interest.

Livingston: You don’t expect to be there forever, you’re waiting for your life to start, so you’re not settling in.

Judge: I was just imagining the wall of my studio apartment when I had my first engineering job. I just put nothing up on the wall.

Panitch: Mike wouldn’t budge. He just wanted the couches and one picture. It was so much about authenticity for Mike, and that’s really where it would have read on film really boring. The lesson is that was the fucking point.

Rappaport: I just remember joking around: “Wow, we’re the first people to make an $11 million movie look like a $3 million movie.”

Suhrstedt: One of the big issues was when Mike learned that he couldn’t get clearance on TGI Friday’s. I remember in an early production meeting Mike really made me laugh, he said, “Well, if we can’t call it TGIF, can we call it Thank Jesus It’s Friday?” It made me crack up. Everyone was like, “No.”

Eshelman: Mike was like, “It’s TGI Friday’s and Chili’s, if they got together and had a restaurant.”

Curry: There were two different restaurants that were supposed to feel almost identical, because all these restaurants looked the same. So we actually filmed them in the same location and divided it and slightly changed it up for each one. They had the same feel.

Judge: We shot it at the Alligator Grill. It’s not there anymore.

Panitch: Chotchkie’s—if you look at the tables in that scene, you could go into one of those places right now and that’s exactly what it would look like.

Eshelman: We actually went to lunch at TGI Friday’s with my assistant, and we measured the stripes on our waiter’s shirt. We had to have the fabric all custom done. All the flair had to go through legal to make sure we could use it.

Stan Gilbert (prop master): Mike plays Stan, the manager, so all Mike kept saying was, “More, I want more, I want more.” So we scrambled all morning long the day of to come up with stuff. We hadn’t asked the right questions, apparently, of how much. [He wanted] 70 percent more flair than I was prepared for.

Judge: I needed more flair.

Suhrstedt: I do remember Mike telling me at the time that the minimum was 15. That was a company rule.

Eshelman: We got all these disposable cameras and I sent them out to some friends of mine that I knew all over the country that worked in cubicle spaces and said, “Will you please take pictures of your coworker?” I was living in Los Angeles and the way people dress in Los Angeles is not indicative of Middle America office cubicle workers. I really wanted to have research that was true and authentic to what people wore.

Klopper: “Bob Slydell.” Just the character names give you an idea of what they should look like.

McGinley: I wanted my shirt to be a size too small because those guys always wear a wardrobe that’s a size too small. Like, maybe they were athletes and now they’re fat fucks and they’re still wearing the fucking ties from high school. I wanted that. I wanted those braided, leather suspenders, which just makes me sick. And I wanted those glasses. I gave [Mindy] that input the week before and I go down to the fitting Monday night to work Tuesday morning and everything she did, she just crushed it. You don’t have to open your mouth and illustrate and demonstrate as much when the wardrobe and the props speak for you.

Bader: We decided on the mullet and then I really wanted the mustache. When I was a kid I really worshipped the album Brothers and Sisters by the Allman Brothers, and when you open it up and just look at the old vinyl, there was a picture on the inside with the whole band, and I just really wanted to be in that picture. So that’s how we decided on the look. It was hard to laugh in that mustache because it was really glued on tightly to my face. Lawrence doesn’t smile a lot because the mustache would have popped off.

Root: The tie on [Milton], it’s just filled with horrendous stains and it smelled. You knew that he never changed, he was not a cleanly person, so you just went by that stuff.

Cole: I had exactly those glasses, not even that long before we did it. I had those big fucking aviators. Early ’90s.

Gilbert: They’re pretty iconic for that period. Mike was very specific about the look he wanted. I was able to show him catalogs of different eyeglasses. The ones for Milton, those were a big deal. Those glasses were so thick that we had to have contact lenses made to counteract the prescription of those thick-ass lenses, otherwise he wouldn’t see and would get headaches.

Root: I had to have contacts and then I’d put on the glasses to see, but I had no depth perception. I had to practice reaching for the stapler, otherwise I’d be off by 3 inches.

Gilbert: That’s my big claim to fame, because I made the stapler. Mike asked me to show him as many staplers as I could. So I went out for several days and scoured the universe for every kind of stapler I could find, from vintage to new to futuristic. He picked out a couple, then he homed in on one, which was a Swingline, but he wanted it to have a bigger hump on the top; he wanted it more bulbous.

I got some Bondo and Bondo’d up a hump and sanded it down and made it as pretty as I could. The mandate was that it would be red.

“Swingline was the only company that didn’t object, [but] they didn’t make [staplers] in any colors other than shades of gray and dark blue. I wanted it to stand out so I said, ‘Let’s make it red.’” —Mike Judge

Judge: I remember hearing we couldn’t clear Boston or Bostitch. I thought they’d want their stuff in movies. Swingline was the only company that didn’t object, [but] they didn’t make them in any colors other than shades of gray and dark blue. I wanted it to stand out so I said, “Let’s make it red.”

Gilbert: I just grabbed a can of spray paint and painted it red. Mike and the production designer say, “OK, we like that, that’s great.” I got permission from Swingline to make a vinyl graphic to put on the side of the stapler, because the logo was [originally] on top. I made a total of 10 staplers.

Judge: People started requesting red staplers. Someone was making a bunch of money on eBay making bootleg red staplers.

Theresa Hardy (Swingline senior marketing manager): The team, at the time, saw it as an opportunity to really capitalize on the cultural movement that the movie did spark, so we were seeing demand for it and decided, why not? We’ve been probably officially making different variations of the red stapler for the better part of 10 years now.

Judge: That stuff was always important to me. There were a couple frustrating things. Somebody decided that Michael Bolton was into little aliens, which I think he absolutely would not be. They put all these little aliens and army men all over his cubicle and I said, “No, let’s get rid of them.” Then someone else, when I wasn’t looking, came back and said, “The aliens are gone, we need to put them back.” We’d already shot two takes, and I was like, “The fucking aliens are back, who put them back?” The script supervisor was like, “No, it’s a continuity error,” so there was one scene where they’re in. The next day we’re shooting there and they’re all back on there again. So this time I took them off myself and went way [over] to another building and threw them into a dumpster where nobody would find them.

Part IV: “It’s Being Present, Listening, and Just Pouncing.”

Despite this being Judge’s first time directing a live-action movie, the script and characters were so detailed there wasn’t a need to deviate much from his vision. Still, he allowed actors and his trusted veteran crew members to suggest ideas and guide him when needed. That led to some indelible improvisational moments and tactically impressive scenes.

David Rennie (film editor): When I saw the first day’s dailies and saw Gary Cole, you’re like “OK, Gary Cole is just fucking brilliant.” This wasn’t about getting it to work, it was about getting it to shine because these guys gave us such gold.

Cole: I tend to make more correct choices when I have some limitations going on—speech pattern, a prop. Lumbergh is basically one speed, he’s taking a Valium and that’s where he is. He’s not going to really rise or fall beyond that.

Root: Gary came in and killed the character because there was an actual guy like that.

Cole: It’s the last moment of telling Milton to go down to the basement in Storage B, and that’s when he finally discovers the stapler on his desk. [Mike] wanted me to take the stapler and—it’s a very little moment and it works—lean over very calmly but then just rip it right out of his hands to see how aggressive he was. Then all of a sudden go back to the Valium.

Root: Mike wanted me to give him a vocalization when he snatched it. I just gave him a “mmm.” You’re taking my toy, how could you possibly do that? I remember Mike standing up next to one of the cubicles and saying [to Gary], “That’s exactly right, what you’re doing, but I want you to elongate the ‘yeaaahhhss.’” I do remember him specifically giving him that rehearsal note.

Judge: I kept adding “yeahs.”

Cole: He would orchestrate additional “yeaaahhhs.” The only thing I was asked to do—which is something he put in the cartoon, it’s the one time he’s reacting badly to something—but all he did was go, “[Breathing in through his teeth.] Oooooohh, no I don’t think so.” I asked if I could add it. It’s the scene where he winds up with the Bobs and all of a sudden they turn the tables and evaluate him.

McGinley: As soon as I said yes [to Mike], I had to film in Toronto with Matthew Perry. I called back: “I’ll play one of the Bobs, I can fly in Monday, shoot Tuesday, Wednesday, Thursday, I gotta be in wardrobe on Friday afternoon.” Mike reconfigured the whole movie schedule to accommodate me.

Riehle: The first day they brought in John and Paul [Willson], I ended up being the guinea pig. They shot the scene of them with me first and the two of them asked Mike, “Is it OK if we riff a little bit?” They were hilarious. We probably spent 15 to 20 minutes doing riffs on it.

Judge: Even if you’re not going to use it, I think you get a good performance when actors feel like they can just say something that comes to their mind in the moment that’s in character. [McGinley] improvised for hours. There was some really great stuff he did with Smykowski. It just needed to get to the point.

McGinley: One of the tenets of improv is that you can’t have two initiators. Paul is a master improvisational person and I’m OK, and we decided I’d be the starter and he’d be the finisher. “Naga, Naga, not gonna work here anymore,” Paul just invented that on the fly. I was stuttering on the name and couldn’t figure out how to read the last name on the script and Paul just closed it. Now it’s an iconic line. That’s all Paul. It’s being present, listening, and just pouncing.

Herman: I had worked with McGinley before. I knew he was going to open up on me. I never broke. He had some hilarious stuff. Mike should put a compilation of stuff he got that day.

Judge: Sanford Panitch, he was just like, “Oh god, you gotta just cut McGinley out of it, you’ve got to stop all these improvs.” David Rennie pranked him actually. He cut together every single improv and made this epically long Bobs scene and brought it over to Sanford’s office and was like, “OK we worked on it a little, what do you think?” Sanford just looked sick to his stomach.

Cole: If this line was improvised, it’s the genius line of all time, which was, “Michael Bolton, I celebrate the man’s entire catalog.” That’s my favorite. He kills me. There’s an energy that he has, it’s pretty special.

Suhrstedt: John probably improvised 100 lines—that might be the only one that made it in there.

McGinley: Dave Herman is one of the most underrated actors on the planet. He’s super present, and no matter what shot you hit, he’s going to hit it back and he’ll probably hit a winner. With “I celebrate the whole catalog,” I was just feeling Dave.

Herman: He would make it as hard as possible. It eventually got into “Not only do I like his music, but the softball videos have improved my game.” There really were these softball videos about hitting for power by Michael Bolton. I do remember [our improv] taking a curve: “Have you seen the softball videos?” and me being like, “No, I have not seen the softball videos, can we please move on?”

Judge: I’d never seen it, but I remember McGinley saying, “Oh no, absolutely, he’s got a softball video.” I was like, yeah, go for it.

Herman: I think at the time Michael Bolton was a perfect target. He had taken himself so seriously and was such a perfect guy to ruin our Michael Bolton’s life. Today he doesn’t take himself quite as seriously, which takes some of the piss out of it.

Judge: When I was working that alphabetizing purchase-order job, I just remember being in some office and somebody just had soft rock playing all the time. Michael Bolton was playing all the time. I’m bad at naming characters. I like giving them normal names. I didn’t want him to have a cool name, and then I just thought, What if I make it a famous person, somebody he hates? In some ways in my mind, this movie is set in 1988.

Naidu: Herman came up with “ass clown,” which is now in the dictionary.

Herman: The original line was “no-singing asshole,” and we had to change that line on the set a moment before “action” because it implied that he didn’t do his own singing, that he was Milli Vanilli. And so it became “no-talent ass clown.” He’s not my cup of tea, but he’s got plenty of talent.

McGinley: I have [never listened to Michael Bolton]. For no reason. I have no skin in the game. I don’t have any feelings. For all I know he’s the greatest guy in the planet.

Michael Bolton (singer): It’s a funny film. I sign a lot of the DVDs for fans. I’m glad I’m secure enough in writing, producing, and Grammys that that’s one of the things people want to do. I sign them “The Real Michael Bolton.”

Livingston: I was really impressed with the way [Mike] handled some of the visual shots, specifically the car crash stunt.

Suhrstedt: That might have been one of the scenes Mike and I talked about in our interview. I remember saying to Mike, “This should be done very simply—you should see this in one shot,” and Mike agreed with me. He said the people from the studio said, “You need to get a whole bunch of cameras and shoot it like an action sequence.” We both thought that’s not funny, that’s not what it’s supposed to be like.

Judge: Originally, Tom Smykowski is writing a suicide note. Then he goes into his car and starts it with the door closed, then his wife unexpectedly comes home, he tries to play it off, and then he backs out, and the camera follows him out and stays there, then we hit the real car.

Riehle: It all depended on this tree in the background and if it was moving. I’d back out and they’d say, “Nope we gotta do it again.” And then each time, just as I got to the spot in the road—everything went at once, the [garage] door, the truck—and then they had to stop it and take me out and put the dummy in to hit the car. Once the truck hit the car they weren’t going to be able to do it again.

Suhrstedt: Mike had said it wasn’t going to be funny when the truck hit the car if the truck and car stayed in the frame—it had to clear frame like a cartoon, which is why it’s so funny. So the stunt guy determined that if he were going to hit the Taurus and push it out of frame, he had to start back a half mile and build up to 60 to 70 miles per hour in this pickup truck.

Judge: The driver of the truck is Chuck Norris’s son. He came down from Dallas to do that.

Suhrstedt: No visual effects at all. We got the dailies back and Mike cut the thing together, and it was just so funny.

Riehle: Mike was calling me into his trailer and he goes, “You gotta see this.” It’s an amazing shot they got.

Suhrstedt: When [Mike] previewed the movie one of the times, he said when that sequence came up it was too much for the audience. So he went back and re-cut it so that Drew is saying, “Hey, did you hear what happened to Smykowski?” And by him telling it and cutting back to it, it took the intensity off it.

Judge: It played in the test screening as sad and dark. I just had Greg narrate. It ended up being even funnier and didn’t bum anyone out because you have this obnoxious guy telling stories. I was proud of that.

Greg Pitts (Drew): I know a lot of the actors were sort of encouraged to improvise. That’s where the “oh-face” thing came up. It was actually a throwback to a girlfriend that I had—my obnoxious self would mimic her face in the moment of orgasm to be funny. She didn’t necessarily find it all that funny. Mike said, “You can just make something up. If you have any ideas, just do whatever you want.” The oh-face was the first one I did, and I remember when I did it for the camera, I could tell by Ron Livingston’s face that it must have been kind of funny. You know when you can sense somebody’s going to laugh and they’re holding it back?

Rennie: I don’t remember how many takes he did, but every one was different. “Going to give you a ride on the bone roller coaster,” was a strong contender, but the oh-face was so funny.

Pitts: Office Space was my first movie, so you don’t know if something is funny if you went off script and tried your own thing until after they yell “cut.” I think [Mike] told me one of the women on the crew fell out of her seat when they screened that scene.

Judge: I did a quick poll around the studio village and people seemed to overwhelmingly love the oh-face.

Livingston: I remember the barbecue scene with Greg being a lot of fun, standing in the ugliest backyard in the world while he disparages Jennifer with a big smile on his face.

Pitts: When we were adding names to who Jennifer Aniston’s character had had sex with, Mike told me, he goes, “Hey, throw the editor’s name in there, Dave Rennie,” so I was like, “Yeah sure.”

Rennie: That’s my claim to fame. We never told anybody and so my friends would see the movie and just burst out laughing in that moment.

Pitts: I remember sitting around getting notes on the scene at Smykowski’s party. [Aniston] was the biggest star in the whole thing and was a huge deal and I was having trouble concentrating on what Mike Judge was saying about the overall theme.

Livingston: You could tell that she was used to people being a little starstruck and intimidated. She immediately tried to diffuse that. It didn’t entirely work with me because I think people sometimes underestimate my capacity for awkwardness, but we were able to muddle through.

Naidu: Jenny was staying at the Four Seasons, and we were all staying at the Hyatt. Although, I loved my room because it had a balcony and no one else did. She had just started seeing Brad Pitt at the time.

Livingston: It was all top secret. We’d finish the shooting day and she would disappear and now I know where she was going.

Pitts: I think there was some mention that PAs had been offered 50 grand to get a picture of the two of them together. I heard a story about them running around Austin trying to catch her dog. It had gotten out of the Four Seasons.

Judge: Boy, that was awful. No one could find the dog. I don’t know how it escaped. I just remember having a very stressful day already and then on top of that hoping to God they found her dog.

Naidu: She was really worried.

Herman: I felt so terrible for her. I had the day off and I remember searching all around the town lake for the dog going like, “I’m going to be the hero, and she’ll name the dog after me!”

Judge: She had to shoot some scene without knowing where her dog was or if it was alive.

Livingston: I remember it got to the point where the local radio stations were talking about it, like, “Come out, everybody help find Jennifer Aniston’s dog.”

Naidu: They put out this radio APB and then Brad Pitt flew down to save the day to go find the dog. They did find the dog. All I recall is “Damn, Brad Pitt is flying down to get the dog!”

Judge: About two years ago, I was checking into a hotel in Austin, and the bellman goes, “Hey Mike,” he introduced himself, “I’m the guy that found Jennifer Aniston’s dog in Austin!”

Part V: “These Motherfuckers Murdered a Printer, Like This Is the Coolest Shit Ever.”

One of the biggest battles that Judge fought against the studio was to make gangster rap part of the soundtrack.

Judge: I had gotten into hip-hop when Run-DMC first came out. I was really into that. Then that whole Dr. Dre, The Chronic, N.W.A, then the Geto Boys—I was just way into that. I just loved the feel of it. I’m obviously not from that world [but] I couldn’t get enough.

Herman: I definitely knew a lot of the rap that Mike was interested in. We have a lot of musical crossovers—Scarface and all the stuff he was thinking about was stuff that I was familiar with. I just thought instantly it was a great idea to have this juxtaposition of hardcore rap with this sterile, weenie environment.

Livingston: That was my introduction to gangster rap. It would basically be Ajay and Dave and Mike just kind of going off. “Did you hear the news on Eazy-E?” I came to all that later.

Naidu: Me, Dave, and Mike had come into it being aficionados. Ron is a gangster in his own way.

Judge: When Boyz n the Hood and Colors came out, I just thought that music over those images was incredible, it was such powerful cinematic music. I hadn’t seen anybody use it for anything but South Central or gangsters. I wanted to use it for something different. I thought it would be perfect for the printer smashing and just as a general backdrop to the boiling anger that’s underneath the surface of these places.

Suhrstedt: I was a little nervous because I’m not well-versed in that music. That’s not my thing. So I listened a bunch with Mike.

Rennie: The first scene that I was really working on was the printer-smashing scene, which was just a bunch of handhelds and guys just smashing the printer. I was sitting there thinking, “What the hell?”

Curry: We had to pick out the field and we ended up having to add some flowers into the background.

Livingston: We kind of went out there with no plan. The one thing I remember is they set the camera up, and Mike was like, “No, it’s gotta be a really low angle,” and Tim kind of rolled his eyes, sort of like, “Uhh, you’ll notice, Mike, that the camera is sitting on the ground; we can’t get any lower.” And Mike was like, “Can we dig a hole?”

Suhrstedt: We dug a hole. The funny thing about that was that wasn’t shot listed. That was something we went into with the awareness of what these hip-hop videos looked like and just kind of winged it on the day.

Gilbert: I went out and found 20 printers that were all the same, because we’re smashing it, right? I took them all apart myself to make them all weaker, so when they hit them with baseball bats, it would come apart. Every take where we broke one and we got more parts, we kept throwing those broken parts onto the inside of the printer.

Livingston: I just walk around in the background with a baseball bat. I wanted it to be the idea that I was blooding these guys a little bit—this was their initiation into this kind of thing. The two of them, all the stuff they did was hilarious.

Naidu: The idea that it takes on the element of a full-on gangster beatdown was very clear to me. I used what little tae kwon do training I had left over and everything I remember from every gangster movie I had. I’d give it a massive hammer kick. That comes from Master Kim when I was 12. Make sure the leg comes above the head.

Herman: I knew this had to be a big, cathartic release scene, a big release for people who lived this life. The more serious it was taken, the more we were letting loose and venting on this thing, and not in a goofy way. I had personal things I was making that printer at that time.

Judge: Dave Herman is smashing a sandbag that you don’t see off camera. At one point I had said, “Can you do one where you just jump up in the air and stomp it as hard as you can?” So he said, “Yeah,” and he nearly severely injured himself. He slipped on it, and it’s on camera, those guys grab him. My first AD said, “OK, Mr. Landis.”

Naidu: I felt really awesome when the stunt guy was like, “Move him out of the way with the bat so you can get at the victim.” I was like, “That’s a dope gesture.”

Rennie: At first I was scoring it like an operatic. I was treating it like a Goodfellas-type thing. And Mike’s like, “No, no.” He always intended the Geto Boys.

Willie D (Geto Boys): [“Still”] makes you want to destroy something. And to mesh that together in that particular scene, it caught a lot of people off guard. You expect to take your coworker outside. These motherfuckers took a printer outside and murdered a printer. Like, this is the coolest shit ever. I loved it.

Naidu: For Mike to [use that music] was the most brilliant contradiction that anyone could have. A “gangster nerd”—that’s most of those kids, they’re feeling like roughnecks out there and going to computer jobs. That’s Mike tapping into the zeitgeist in a prolific and prophetic way.

Rappaport: Even 20 years later I want to throw my printer out the window.

Rennie: I had happened to see Out of Sight, the [Steven] Soderbergh movie, that weekend. It’s a great movie, but there was certain style to it—the freeze frames—that I found was a little bit over the top. So just for fun, I thought “OK, what if I tried slowing these things down and trying some speed changes and things like that just to mess with it, just to see what would happen?”

Judge: We over-cranked the cameras. There’s multiple attempts at editing that, it went all over the place and we finally got it dialed in.

Cole: You see the camera just back away as if they’re done. And then Herman just wrangles out, just throws his elbows out of their grasp and returns to the printer to beat it again.

Herman: Most of the stuff that we did was improvised on the spot. It was “How can we make this as violent and old-school mafioso, Goodfellas, Robert De Niro style [as possible]?”

Cole: And then they’re dancing.

Naidu: I’m a break-dancer, and I had an Indian break-dance crew that I was hanging out with every night in Austin. That break-dancing thing happened because Mike said, “Use the space.” So I came out and did a swipe and they were like “Oh, that’s staying in.” When we’re coming out of Peter’s house, I remember asking Mike what song he thought might be playing, because I wanted to be singing it coming out of there. That’s how “back up in your ass with a resurrection” came up.

Willie D: We actually did an Office Space–Geto Boys tour in 2015. We had some office furniture on the stage and part of it was we had a printer and we smashed the printer with the bat, so we reenacted the scene with the music.

Naidu: One time I was standing out for this audition in New York, and this big, scary-looking Goodfellas dude across the way at a cigar shop was like, “Hey, come over here.” I was like, “Oh shit, what’s going on?” He brought me in and there were all these rough-ass dudes like, “Ohh, it’s him.” He was like, “Shut up, guys. Listen, I just want to tell you, kid, we think the way you did the printer was very authentic. You need anything ever, you just come see us.” Doing that scene did have fringe benefits in my real life.

Judge: When I first heard [“Damn It Feels Good to Be a Gangsta,”] I thought, “This should be in the movie.” I just loved the feel of it. Kind of a mellow vibe that inspired the scene. It feels like this sort of release.

Livingston: There was one scene, it’s just in that montage, where I’m going fishing, and it was this bit where I’m leaving the office. Gary sees me and sort of steps to intercept me. A lot of movies would make that the big showdown: “I’m not going to take this anymore.” What we did was just move imperceptibly around and to the left, as if he wasn’t there anymore, the path of least resistance. I think there’s a lot in this movie about “follow the path of least resistance.”

Willie D: There’s two times in a person’s life that they can experience something like that. One is when you are basically having a moment and you feel like a gangster. The other is when someone has pushed you to the brink, and you’re like, “Goddammit, I want some respect.”

Judge: We’re out at Lake Bastrop. We had to have the Humane Society there to make sure our fish weren’t hurt. Right next to us there are people catching and gutting fish. “Y’all making a movie?” There’s the Humane Society making sure these two Hollywood fish don’t get harmed.

Gilbert: The only animal that I ever killed and ever cleaned in my entire life, still to this day, is a trout. There’s only one way to do it properly, so I had to train Ron how to do that, how to slit up the underbelly and put your fingers in the gills and rip it all out.

Livingston: He taught me very well. It was very simple. You just grab here and pull. I was like, “OK.” I think we got it on the first take. I don’t think I’ve [gutted a fish since].

Willie D: Fox didn’t want the music in there. Mike had to fight for those songs to be in the scenes. They had to actually do a focus group to get the music in there. Now that you hear it, nothing could have been more perfect.

Herman: They were trying to get rid of it. They were trying to get Chumbawamba.

Judge: Tom Rothman said, “You’ve got to get rid of that gangster rap music.” His argument was “I want the movie to be fun.” I said, “I think that is fun.” He said, “It’s too dark and angry.” He kept insisting. I did something I should not have done, but it worked out really miraculously. I said, at the next test screening, if the focus group doesn’t like it, then I’ll take out the music. At the test screening they have 20 people afterward, they were like 18- to 25-year-olds, and this woman who is the moderator is asking a bunch of questions and then gets to the point. She makes a sneering face, she goes, “What did you guys think of the music?” Kind of like, “Ew, wasn’t that bad?” All 20 of them go, “Oh, the music was great!” She’s like, “OK, but what about the gangster rap?” She’s just trying so hard to get one negative comment and they would not give her anything. “But maybe there was too much of it? Maybe it was little too profane with the ‘Die, motherfuckers?’” This kid who was 19, he just says, “No, but that’s what’s great about it, they’re these geeky white boys in cubicles, but the music is angry because they’re angry.” I looked over at Rothman and he just gave me a shrug like, “OK, you win.”

“If Mike is fighting for some shit, I’m probably going to say he’s fighting for the right thing. When it comes to comedy, Mike Judge is batting 1,000. I ain’t seen a miss yet.” —Willie D

Willie D: If Mike is fighting for some shit, I’m probably going to say he’s fighting for the right thing. When it comes to comedy, Mike Judge is batting 1,000. I ain’t seen a miss yet.

Rennie: I think the reason Mike prevailed so much on these things is ultimately it was so low budget—I think the studio felt like King of the Hill was just starting up and so they wanted to keep him happy. They figured this is a mess, who cares? It’s a low-budget movie, fine. They didn’t realize at the time what they had.

Panitch: I think what it speaks to is being ahead of its time. Now, of course, you wouldn’t even think twice about that. Now you want to put something like that in the movie for it to be as relatable as possible. I think that’s the gift of Mike Judge. He saw where the culture was going.

Judge: If one person had said anything negative, the music probably would have not been in the movie. Thank god for the 19- to 25-year-olds in that focus group.

Part VI: “It Looked Like a Big Bird Movie.”

With a mostly unknown cast and subtle, specific humor, Office Space wasn’t the easiest sell. The movie’s poster, later lampooned, featured Milton hiding behind an anonymous employee covered in Post-it notes. The movie grossed $10.8 million at the domestic box office, just barely edging the cost of production.

Rappaport: Fox was not sure how to market this.

Herman: I’m not quite sure how you market this movie. If you were to say, “Here’s this really dry take on how passive-aggressive workspaces are,” I don’t know how you go, “Come on, see it!”

Panitch: Honestly, I do feel for the marketing guys because I was in meetings where they were like, “How on earth are we going to convey this movie in a poster? Are we going to put in four guys that nobody recognizes? Or just a weird guy with glasses in a darkened office?” In all fairness, it wasn’t an easy film to be reductive with. Try to close your eyes and imagine a one sheet for Office Space. It’s really challenging.

Rappaport: We didn’t have a better idea. I just remember all of us saying, “Oh god, the Post-it note guy?”

Judge: My first reaction was “This looks like an ad for Office Depot.”

Panitch: Mike and I were in the same boat. We both hated the Post-it guy. And there wasn’t anything either of us could do about it. I wasn’t high enough on the food chain to make those kinds of decisions.

Livingston: I’m an unknown, so it doesn’t make any sense to put me on a poster. But I wasn’t sure why they were putting somebody that was supposed to be me and covering him with Post-it notes. I didn’t quite understand what that was.

McGinley: It looked like a Big Bird movie, like an R-rated Big Bird movie.

Root: Mike decided Milton was such an important part of that movie he wanted to eventually see some image of Milton. Originally, I wasn’t peeking behind him, it was just the Post-it guy image, and then Mike said, “No, I want Milton in there so you can see him.”

Judge: I remember having these arguments, and they kept thinking that I was trying to make the poster true to the movie. I would say, “I don’t care if you lie and say Tom Cruise is in it, this isn’t helping us.” I think they wanted to paint me as this sensitive indie filmmaker, which I wasn’t at all.

Herman: I know that during the middle of the movie, somewhere there were rumors, mumblings that they were looking for a PG-13 rating. I was like, “I’m going to curse a blue streak every scene I have.” This is for people who are living this. That’s who is going to see this. I gotta have a hand in getting this at least an R-rating.

Rappaport: This was one of those movies where word of mouth was the best marketing you were going to have. We probably should have recognized that and figured out how to do a ton of screenings. At the time, if you wanted to market a movie, you bought commercials. There was no internet.

Panitch: It just didn’t lend itself to traditional 30-second television spots at the time.

Cole: When they released, I said, “This is not a prime release date. This is a wasteland, really; this is the end of February, this is not when you bring out your big guns.”

Suhrstedt: I remember thinking, “Well, they’re not really getting behind the movie.” I knew that it was good. I do remember that I anxiously read the reviews, I heard there were great reviews on the radio that morning.

Roger Ebert (Chicago Sun-Times film critic): Office Space is a comic cry of rage against the nightmare of modern office life. It has many of the same complaints as “Dilbert” and the movie Clockwatchers and, for that matter, the works of Kafka and the Book of Job. It is about work that crushes the spirit. Office cubicles are cells, supervisors are the wardens, and modern management theory is skewed to employ as many managers and as few workers as possible.

Rappaport: My current wife, then girlfriend, went to a couple of theaters on Friday night and it was so depressing. There were two people in the theater. Welp, there goes that movie.

McGinley: It fucking tanked, it was a dog with fleas, nobody fucking went. It was two weeks and out. I was like, “I’ll be goddamned. You motherfuckers, you were on the 5-yard line you couldn’t put it in,” and I couldn’t fucking believe it. Whoever the marketing geniuses were at the studio, they fumbled on the 2, man.

Bader: I can’t explain to you how upset I was, because I thought this was as close to my taste as any movie could possibly be. I really like every frame of this movie, every joke lands, and yet no one is seeing it. It’s a total bomb. I was really, genuinely upset. As a consequence of that, I didn’t see the film for another 10 years.

Judge: I was really bummed out, because I had fought so hard for all these choices, and when the movie doesn’t do well right away, there’s sort of a “I told you so, maybe next time you listen to us.”

Herman: Somebody said it made $7 million, and I was like, “That’s great!” He was like, “No, $7 million is bad!” I still pride myself on not knowing anything about the business end of this stuff.

Judge: [But] Tom Rothman and Sanford wanted me to do a movie again. After opening weekend I got a bunch of calls. Jim Carrey, who was one of my heroes, he wanted to meet, he loved it; directors like David Zucker; Madonna called and liked it. Chris Rock left me the best voicemail.

Panitch: I do remember focus grouping, and that was part of what was frustrating about the box office—we knew people loved the movie, and we loved the movie, but we just couldn’t seem to find a way to get wide audiences to go to the theater and see it.

Livingston: They were trying to reach the There’s Something About Mary audience, and it just didn’t happen.

Panitch: It just wasn’t an audience that traditionally went to movie theaters. Thank god for home video in the world.

Part VII: “Are People Coming Up to You About This Movie?”

After a swift exit from theaters, Office Space started finding its audience on VHS and, eventually, on DVD. It became a staple rerun on Comedy Central two years later, as the network aired the movie more than 30 times over the next couple of years. By 2006, DVD sales had reached $6 million in the U.S., gaining the word of mouth traction it hadn’t achieved prior to its release.

Rennie: I think part of the definition of a cult classic is a really good movie that isn’t marketed well. It has to find its audience organically.

Livingston: I think it was perfect the way it happened, because part of the reason the movie’s had such an enduring appeal is everybody feels like they discovered it and introduced it to their friends. It’s not something that was shoved down your throat or that you were told you were supposed to be excited about. Everybody discovered it on their own.

Cole: A year later I was doing a play in Chicago, and I’m walking down a street and somebody yells across the street, “Did you get the TPS report?” And I went, “Jesus, OK. The one person who saw the movie.” But then this began to happen on a daily basis. People were coming up to me and going, “Yeahhhhh.”

Bader: My wife and I were driving downtown, and these two guys in a pickup truck with tats all over pulled up next to me. The guy looked at me and then nudged to his friend who was driving. They both look over and they go, “Hey what would you do with a million dollars?” And I said, “Two chicks at the same time, dude,” and they laughed like hell. I turned to my wife and went, “Office Space—I wonder what’s happening?”

McGinley: To this day people bark some of that shit at me. It’s the first big-hit comedy I got to be in. And then it was like, “Oh, McGinley can turn a joke.” I’m like, “Yeah, fuckface, what did I tell you?”

Root: Richard Riehle and I would see each other in auditions. “Are people coming up to you about this movie?” And we would tell each other stories of people going insane for this movie.

Riehle: A friend of mine invited me to a cigar club that he belonged to in Beverly Hills. Two or three girls were looking for a restroom. They ran into us and they said, “Were you in Office Space?” I said, “Yes.” “Can we get your autograph and can you put down your line about the stapler?” And I said “You know, I really was in Office Space but that’s Stephen Root—but I will give you an autograph.”

Eshelman: I worked with [production designer] Ed McAvoy on a movie later that took place in a college, and he said it was so funny because he was doing a scout going down a hallway and people were playing Office Space in their rooms.

Bader: After three years of no residual checks, I started getting these huge checks. I was like, “Oh my god, what’s going on?” It was Comedy Central, and the DVD sold really well.

Klopper: When it came out on DVD, it became one of the largest DVD rentals in Fox history. What that said was, to me, it wasn’t the right kind of movie for a huge studio to market. If Fox Searchlight had existed at that time—it needed a smaller arm that knew how to handle it.

Rennie: When Mike and I were doing Idiocracy, which was [seven] years later, I think I heard that Office Space was in the top five DVDs of all time for 20th Century Fox. It was an amazing statistic. Crazy. I remember one of the people at Fox high up who didn’t really understand Office Space, he saw Mike on the lot and said, “Mike! Office Space. Who knew?!” Well, we did!

Judge: I was at lunch and Tom Rothman comes over and says, “Have you seen what this movie’s doing?” He just kept going “Who knew? Who knew?” I was thinking like, “Well, I kinda knew.”

Panitch: The idea that a film could become profitable based on its ancillaries is an unusual thing.

Naidu: That spoke to the whole new wave of movies being made. I think it’s life-affirming that when something’s good, it can have a life regardless of whether or not it plays out at the box office.

Cole: I heard stuff like people in offices on Friday, instead of going to happy hour, would buy a bunch of booze and go to somebody’s place and run the movie. It kept going on. They were doing midnight showings of Office Space like they used to do Rocky Horror Picture Show.

Bader: It’s an odd legacy, but if you Google “two chicks at the same time” my picture comes up. That’s my contribution to our culture as a whole. I guess I could have done without people shouting it out when I’m at the grocery store with my 4-year-old daughter. But it comes from love.

Part VIII: “It Was an Existential Experience for People.”

Twenty years later, the movie remains razor sharp in its critique of corporate America, speaking directly to the plight of the cubicle lifestyle and inspiring an aesthetic that’s saturated numerous commercials, television series, and movies over the past two decades.

Rappaport: I think anybody who has ever worked in an office identifies with this movie. Mike captured the universal experience—the annoying boss, the annoying printer, the annoying coworker, the dismal environment, the cubicles.

Herman: Mike hit on these universal things that seem so simple upon first viewing. “Oh yeah, traffic, oh yeah, the static shock.” They seem so simple but they’re these universal truths.

Judge: Occasionally people will tell me they quit their job and found a new career. Sometimes that’s a little heavy—I didn’t want people to quit their jobs. But I do get that, and it’s always really nice.

Root: There have been movies about offices—go to The Apartment—but not the drudgery, not the sameness, not the mind-numbing condition of the ’50s. That’s where everybody was supposed to be conforming, looking the same, and that continued to go throughout the century. Nobody had done an in-depth study of the drudgery and sameness of what office life can be. That was the true precursor.

Naidu: That particular Office Space style is a part of our landscape in terms of storytelling. It’s the window in which you look at it, not just what the characters are up to. The camera has to frame it as “Oh shit, there’s no escape.”

Panitch: The Office as a TV show—why does that work as a British TV show, converted into an American show, which is now still one of the biggest shows on Netflix? There’s an odd thing about office environments being hugely relatable to the world. I think that’s the thing about this movie. It’s utterly true in its own absurdity. How is it possible 20 years later people are still quoting this little movie? I think that’s why.

Judge: When they were doing the American version [of The Office], they sent it to me to see if I was interested. At the time I’d just had a bad experience doing a pilot with Fox and said no thanks. It didn’t help that the packet they sent to me [was] the review of the British Office saying “The Office succeeds where movies like Office Space failed.”

Herman: Every commercial break, there’s at least two commercials that look like Office Space and it’s really sustained this life that has transcended all that. It was an existential experience for people who are in the midst of that life. You look at it and go, “Oh my god, that’s what I’m doing, I’m doing that right now.”

Rappaport: I’ll look at shots in commercials with a bunch of cubicles and the angles they’re using, and I’m like, “That’s right out of Office Space.”

“Dave Grohl told me Office Space changed his life. I didn’t get into the details of exactly how.” —Ron Livingston

Livingston: Dave Grohl told me Office Space changed his life. I didn’t get into the details of exactly how.

Dave Grohl (Foo Fighters lead singer): All over the world, every band I know, their favorite tour-bus movie is Office Space.

Hardy: Every new [Swingline] employee actually gets a red 747 stapler on the first day, and then anyone on my team is required especially to watch the movie. And it’s funny, on one of the fridges in our cafés is a quote from the movie that says “Excuse me, I think you have my stapler.”

Livingston: If people have me sign their DVDs, [“Fuckin’ A, man”] is usually what I put on it, because I think it’s a great anticlimactic way to end the movie that doesn’t take itself too seriously, but gets to the heart of it.

Willie D: I just know that I never want to work in an office. I never want to work in a 9-to-5 setting where somebody’s bossing you around. Just having somebody standing over you, bossing you around, that’s the thing that made all those guys finally snap. The structure, the monotony, I think that drives people crazy.

Judge: I’m doing a show [Silicon Valley] about the tech world. Now, they’ve gotten rid of cubicles. They all brag about their open work space: “It’s all open.” I think a lot of people want cubicles back. People want some privacy. I think people try to keep dressing up work as something that’s not work. I think that’s almost more annoying than just the work itself. That’s carried on since Office Space came out. In general, no matter how workplaces change, human beings will find a way to be annoyed by other human beings.

Livingston: The movie, at its heart, is about a guy who is miserable doing all the things he’s told he’s supposed to be doing. And really, the only thing that happens in the movie is he gives himself permission to do those things and to try to figure out what does make him happy. There’s something about that that’s timeless. It goes against everything we’re taught. “Don’t quit.” “Make the best of a bad situation.” It’s something that really resonated and still resonates. It makes people feel empowered about their lives.

Rappaport: We’re all still trying to figure out: What’s the right way to care a little bit less?

Livingston: Fuckin’ A, man.

Jake Kring-Schreifels is a sports and entertainment writer based in Washington, D.C. His work has also appeared in Esquire.com, GQ.com and The New York Times.