‘Office Space’ at 25: The Unlikely Cult Hit That Had Its Cast “Biting the Inside” of Their Cheeks From Laughter

Office Space is celebrating its 25th anniversary following its delayed path to success, although hopefully no one would get their ass kicked for saying something like that.

Released Feb. 19, 1999, director Mike Judge‘s enduring and endlessly quotable workplace satire follows computer programmer Peter Gibbons (Ron Livingston), who decides to stop caring about his day job and teams up with Initech co-workers Michael Bolton (David Herman) and Samir Nagheenanajar (Ajay Naidu) to defraud the company. The Fox comedy — featuring such on-the-rise performers as Jennifer Aniston, John C. McGinley, Gary Cole and Stephen Root — collected just $10 million at the time but became a cult favorite after finding a following through cable and home video.

Other standouts from the cast include Richard Riehle as engineer liaison Tom Smykowski, who defends his job (“I have people skills!”) to Paul Willson and McGinley as the two Bobs who are put in charge of layoffs. In separate conversations with The Hollywood Reporter, Herman (Bob’s Burgers, The Great North), Riehle (Free Willy, Grounded for Life) and Willson (Cheers, It’s Garry Shandling’s Show) discuss the iconic lines that were last-minute additions, tensions with studio brass, the film continuing to resonate, and how its slow-burn trajectory impacted both residual paychecks and typecasting.

How does it feel to hit 25 years since Office Space?

Richard Riehle (engineer liaison Tom Smykowski): Hard to imagine it’s been that long. It seems like just yesterday, and people still talk about it. When I’m recognized, it’s one of the first things they ask about.

Is there a certain line that fans bring up?

Riehle: They like the “Jump to Conclusions” mat, of course. There’s lots of questions about if I have the mat and where it is. I don’t have it. I don’t think anyone knows where it went. It disappeared.

How did you get involved with the film?

David Herman (Michael Bolton): I had been doing King of the Hill, so I knew Mike [Judge]. He must have given the script to me prior to the initial table read, which was several months before production started, and it was a totally different test cast at the time. I guess he did have me in mind for the role.

Riehle: The Office Space script was absolutely hilarious. The first time I went in, they had me reading both for the psychiatrist and for Tom Smykowski. Fortunately, the next two times I came in, they had already found their psychiatrist with Mike McShane, so I was reading for Tom.

Paul Willson (One of the Bobs): I went out to Lionsgate for an audition that I didn’t get. But the casting director for Office Space saw me in the hall and said, “You should read for this.” I had a callback and then nothing, which usually means you didn’t get it. A month later, my agent got a call saying they decided to go with me because they had to switch up the schedule, and the guy they cast as Bob had a preexisting contract at a theater in Chicago. Because of the change, what had been a three-week shooting schedule for my character became one week.

Riehle: Mike [Judge] always had things that he wanted to throw in — “Try this, try that.” He was the best host there in Austin, as well as director. He would take us to places where his band used to play and to places with good food.

Herman: It was much later that I found out that he really had to fight for the unknown actors he used. These are all stories I heard about secondhand, but I think Fox was hoping to get Matt Damon and Ben Affleck. I certainly didn’t know at the time.

Willson: Mike and I got along well. During the shoot, sometimes he micro-directed, which comes from his sense as an animation director. He wanted certain looks, and if you notice, the whole movie is pretty spare in terms of set decoration. He likes to have a clean frame, so it’s easier to focus on what’s supposed to be funny. I don’t think there was one joke that falls flat in that film.

Which memories stand out from the shoot?

Herman: The studio was not happy with the dailies as the movie was being made. They were hoping that people would smile more during the movie or get kicked in the balls more. But I do remember being told that they were going for a PG-13 rating, and I took it upon myself to curse a blue streak. I just felt like, this movie is not for kids, and not because it’s dirty, but it’s for people who have lived this passive-aggressive workspace. It got an R-rating, and when you look at why on Common Sense Media, it’s due to language. It’s my language — it’s my additions.

Willson: I got to set right when Phil Hartman had been killed by his wife. Stephen Root had worked with him on NewsRadio, so he was a little sideways for a bit.

Riehle: Mike was always good about letting people find their way through what he was trying to get. In my scene with the Bobs, I was biting the inside of my cheeks a lot because the two of them were hilarious, both in the improv leading up to it and in shooting the actual scene. Mike allowed them to go far afield in finding out their relationship and how they were going to interrogate people, but then it would always work its way back to the script, which Mike had absolutely fine-tuned.

Herman: My original line about Michael Bolton was, “He’s a no-singing asshole,” and we changed it to “no-talent ass clown.” There was something legal about, if you say he’s no-singing, the connotation is that he’s Milli Vanilli and not actually singing. “Ass clown” really entered the vernacular because of the movie.

Willson: [When Bob botches Samir’s name,] one improvised false start was starting a motor scooter (makes an engine sound that resembles Samir’s last name), but that didn’t work. But I’m particularly happy to have then improvised “Not gonna work here anymore, anyway.” I felt like the second-stringer who actually scores a touchdown. And then at an anniversary screening in Austin in 2009, Mike got up and thanked me for that “not gonna work here” line, and the audience cheered.

Herman: There was a big stink from Fox about the music, which is so hilariously wrong. The fact that there’s gangster rap throughout it adds such a tremendous dimension to the movie, that you juxtapose these lives with gangster rap. But if you look at the trailer, the music they used was Fatboy Slim. That’s the music they wanted in it.

Richard, the trailer also includes your character in his cast after the car accident. What was that like to play?

Riehle: The car wreck was really tricky to shoot. It all depended upon this little tree in the background, and I can’t remember whether it had to be moving or not moving. We did six takes that weren’t going to work out, and so they would cut, and we’d do it again. Then they took me to makeup, and they didn’t have anyone to put me in the cast and the halo [brace], so they had hired an actual EMT. Then he had to leave, and he handed a cast cutter to one of the PAs and said, “When you’re done, cut this off.” (Laughs.) I was stuck in the cast for about six hours.

Willson: Mike showed me that scene on a daily, and I said, “Wow, how’d you do that?” (Laughs.) Every time I watch the movie, and Tom backs up out of the garage and gets T-boned, I’m taken by surprise.

Richard, what was it like to reconnect with Jennifer Aniston, given that you starred with her on NBC’s Ferris Bueller sitcom in the early ’90s?

Riehle: She was great, and nothing ever changed. One time, I was working on ER over on the Warner Bros. lot, and I went into the commissary to grab a cup of coffee. She was there with a bunch of the Friends actors and made a point of coming up and saying hi and introduced me to all of them. That was the case when we were in Austin — no special demands. She couldn’t have been a better person.

Herman: I had gone to high school with Jennifer Aniston. In fact, during the Office Space 20th anniversary, she made public that she had a crush on me in high school. She’s really an exceptional actress.

Do you remember the first time you saw the film?

Riehle: I was doing a Broadway show, and I saw it on my Monday off after it had just opened. I was nervous about how the New York critics would receive it, and they all loved it. It was a pretty full house for a Monday matinee, and everybody was laughing, and I was right there with them: “This is terrific.” I went back to the show on Tuesday and said, “Next Monday, I’ll go see this movie again. We’ll all enjoy it.” And it was gone. It played literally one week, so most people didn’t see it in the theater. It had something to do with Fox having only rented the theaters for one week.

Willson: I went to see it at a theater in a mall in the first week, and that was the last week. Apparently, Fox did not believe in the film. They pretty much only promoted it on Fox outlets.

Herman: I don’t know that there’s a right way to market this movie, and that’s because it’s a really, really good movie. You go, “Here’s this dreary life. Come watch it on the big screen.”

Riehle: Maybe four months later or so, I was back in L.A. and doing upfronts with Fox, so Mike was there as well, and I said, “Mike, the strangest thing is happening. People on the street are quoting lines from Office Space to me.” And he said, “It just got picked up on Comedy Central, and everybody is loving it.”

Willson: What this did was make it possible for me to make so much more money from the movie than I would have made. You don’t get residuals for a feature film that’s released in theaters, but you sure do for video and everything else.

Riehle: It certainly was a nice element. Unfortunately, it was sold outright to Comedy Central, I think. I never found out any of the details of that. But I’ve gotten more checks over a longer period of time for Free Willy than I have for Office Space. (Laughs.) But it certainly has been nice to get definitely a decent check for it a couple times a year.

Herman: I don’t know that the residuals are any different from things I’ve done that are unsuccessful, so it hasn’t changed my life.

Did the movie lead to typecasting?

Herman: That happened. It was like, “Let’s get him to play other nerds.” I was like, “I don’t want to do that. I’d like to play King Lear, so please offer me King Lear.”

What do you credit for the enduring love of this film?

Herman: It’s the universal nature of the observations, and the economy in which it’s done, that really is the reason why it’s enduring.

Riehle: People would watch it and then tell each other, and it really was offices. People who worked in offices would quote something in it, and when somebody didn’t respond, they’d say, “Oh, you gotta watch this movie.” That’s how it evolved, and it’s continued. It’s really remarkable.