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What The Cast Of Office Space Is Doing Now

Released just before the dawn of the new millennium, Mike Judge's dark, edgy comedy Office Space is still regarded as one of cinema's best workplace comedies. Set within a fictional software company called Initech, Office Space explores the unique insanity of paper-pushing through the viewpoint of three programmers who just can't take it any more. Together, they concoct a plan to quietly steal from the company so that they never have to return to work again.

Judge's pitch-perfect script and direction made Office Space a cult classic that resonates to this day. Who knew we all needed to see a printer destroyed with a baseball bat so badly? Judge's vision is taken to stratospheric heights by the killer cast, which features everyone from sitcom stars to legendary character actors. Unsurprisingly, the stars of Office Space have gone on to lead fascinating careers since the film's release. We're here to see what they've been up to, beyond the cold, clinical walls of Initech.

Ron Livingston

The entire plot of Office Space hinges on Peter Gibbons, played by Ron Livingston, an apathetic programmer looking for a big change in his life. After undergoing hypnosis — and watching his psychiatrist die in front of him, in the middle of the session — Peter gains a new lease on life, in which he cares a whole lot less about his job. Eventually, he barely even goes into work at all, wantonly skipping days at a time. When he does show up, he guts fish on his desk, removes entire cubicle walls, and steals his boss' parking spot. Eventually, he works out a plant to quietly steal money from Initech — which, naturally, goes awry. In the end, however, things work out for Peter, who he gets to live out his life with much more freedom than he had at Initech.

Ever since Office Space, Livingston has remained a familiar staple of the big and small screen. Livingston broadened his horizons with radically different roles in films like Adaptation and The Cooler. He also picked up roles on HBO series including Boardwalk Empire and Sex and the City, the latter of which saw him gain infamy as Jack Berger of the infamous break-up Post-it. 2018 was a particularly big year for Livingston: He appeared in Tully, The Long Dumb Road, The Professor, and the fabulously named The Man Who Killed Hitler and Then the Bigfoot.

Gary Cole

As the droning, dull, and irritating Bill Lumbergh, Gary Cole is an infuriating marvel. Who else could make the phrase "TPS reports" as odious as he manages to? Peter's hatred for Lumbergh spurs his vengeful fantasies, his plan to steal money from Initech, and his brief breakup with Joanna, his love interest. Eventually, however, it is Lumbergh's dismissive treatment of Milton, Initech's most overlooked employee, that results in his downfall. Peter's freedom is a happy accident.

Lumbergh is definitely one of Cole's most popular roles, but the celebrated actor is also beloved for his work on shows like True Blood, Chuck, Entourage, Mixed-ish, and The Good Wife. As far as the big screen goes, Cole has appeared in films including Blockers, Tammy, Pineapple Express, and Talladega Nights: The Ballad of Ricky Bobby. His most high-profile role in recent years is definitely political advisor Kent Davison on Veep, which earned him multiple Emmy nominations. Cole is also a heavyweight voice actor, beloved for playing Harvey Birdman in Adult Swim standard-bearer Harvey Birdman: Attorney at Law.

Jennifer Aniston

Office Space is filled with characters who are unhappy at their menial jobs, and Jennifer Aniston's Joanna is no exception. A waitress at Chotchkie's, an obvious parody of American chain restaurants like TGI Fridays, Joanna is constantly chastised for her lack of "flair," referring to sets of ridiculous pins meant to adorn each employee's uniform. After watching Peter flaunt his freedom, Joanna is inspired and finally quits her job ... but unfortunately, their relationship falls to pieces when Peter finds out that Joanna once slept with Lumbergh. Thankfully, it's not Bill Lumbergh, but somebody else entirely, and Peter and Joanna reconcile.

By the time Office Space hit theaters in 1999, Aniston was already a television fixture thanks to Friends, in which she starred as Rachel Green. After Friends came to an end in 2004, Aniston split her time between big Hollywood films like Bruce Almighty, We're the Millers, and Horrible Bosses, and smaller indies like Cake and The Good Girl. 2019 saw her make waves when she took on a starring role in Apple TV+'s flagship series The Morning Show as trailblazing anchor Alex Levy. This earned her a Golden Globe nomination, as well as a Screen Actor's Guild Award for Outstanding Female Actor in a Drama Series.

Stephen Root

Despite being the most forgettable person at Initech, Milton Waddams, played by Stephen Root, is definitely one of Office Space's most unforgettable characters. A mumbling, struggling, low-level employee who's constantly shoved aside and overlooked, Milton gets the short end of the stick time and time again. Ultimately, however, Milton gets the last laugh: He burns down the building after stealing several traveler's checks — left behind by Peter as an apology for stealing the money in the first place — which are worth a fortune. Milton ends the movie on a fabulous Mexican vacation, free, at last, from people stealing his stapler.

A lesser actor's career might have begun and ended with Milton. But Root's sheer talent and incomparable work ethic have made him one of the best character actors currently working in Hollywood. After wrapping up a long-running stint as Bill Dauterive and Buck Strickland on King of the Hill, Root went on to appear in acclaimed films like Idiocracy and Trumbo, and eventually became a favorite of the Coen brothers, appearing in everything from O Brother, Where Art Thou? to No Country for Old Men. Recently, you might have caught him in a scene-stealing supporting turn in Get Out, or as an assassin's handler in HBO's hit comedy series Barry.

Diedrich Bader

Office Space is full of out-there characters, but one of the strangest has to be Peter's eccentric neighbor Lawrence, played by Diedrich Bader. As two men who live in an apartment complex with exceedingly thin walls, Lawrence and Peter can't help but keep in touch. Ultimately, after Peter frees himself from Initech for good, he goes to work with Lawrence at a construction site, and finds himself to be truly happy, working outside with one of his friends.

Bader has played a whole host of great comedic and dramatic parts throughout his career, including turns on television shows like Better Things, Arrested Development, Bones, Veep, and Two and a Half Men. He's also a prolific voice actor: Bader starred as Batman himself on Batman: The Brave and the Bold, portrayed another DC headliner as Guy Gardner in Green Lantern: The Animated Series, and brought strange, lovable Judah to life on BoJack Horseman. Bader currently stars as General Rongley on the Netflix original comedy, Space Force.

David Herman

As you might have noticed, Michael Bolton, an unassuming programmer played by David Herman, just so happens to share a first and last name with a famous crooner. When two supervisors come to visit Initech to figure out where they can make cuts for an eventual downsizing, the issue of Michael's name comes up time and time again. Eventually, the constant refrain is enough to drive Michael into joining Peter's harebrained scheme. He refuses to change his name — as he memorably decrees, he shouldn't have to, as the other Michael Bolton is "the one who sucks." 

Believe it or not, Herman almost didn't get to play Bolton at all. He had a recurring role on MADtv at the time, which was eating into the time he wanted to devote to King of the Hill — and so Herman tanked a table read and got himself fired. Herman then came across the script for Office Space, and history was made. Herman went on to appear in other Judge projects like Idiocracy as well as television shows like 24 and Better Things. His career as a voice actor has continued as well, with appearances on Brickleberry and Bob's Burgers. These days, Herman is still an active performer, appearing on series like Central Park, Bless the Harts, and Paradise PD.

Ajay Naidu

The scheme to rob Initech can't be pulled off by Peter alone: He can only accomplish the con alongside Michael and Samir Nagheenanajar, played by Ajay Naidu. Once Samir and Michael decide to help Peter, they're all in, especially since both Samir and Michael are set to be fired during the company's downsizing. Seeing Samir vent his rage is truly something to behold — the man can wield a baseball bat like no other.

After appearing in Office Space, Naidu worked steadily for a number of years. On the big screen, Naidu appeared in projects like K-Pax, Requiem for a Dream, Bad Santa, and The Wrestler in small roles. He built up his resume with bigger supporting turns on the small screen, including stints on 30 Rock, The West Wing, Friends from College, Bored to Death, and Blindspot, as well as voice work on King of the Hill alongside other Office Space alumni. Over the years, Naidu has also built up a robust career in New York's theater scene, working with talents like the late Philip Seymour Hoffman and Al Pacino.

John C. McGinley

As one of the two "Bobs" who arrives at Initech to help decide who will stay and who will go, John C. McGinley is pivotal. Endlessly cheerful on the outside, McGinley's Bob is actually as merciless as he is chipper, quietly firing people as he makes friends with them. However, he takes a big liking to Peter — an unexpected side effect of Peter's newfound, anti-establishment attitude. Bob ends up using Peter to try to figure out how to overhaul Initech.

Any comedy fan worth their salt probably knows McGinley best from his long-running role on Scrubs as Dr. Perry Cox, the brutal yet secretly big-hearted mentor to Zach Braff's John "J.D." Dorian. McGinley isn't just good for a laugh, however — he's also played major roles in famous dramas. Film buffs might recognize McGinley from his roles in Platoon and Wall Street, in addition to more recent films like 42 and Battle of the Sexes. In addition to Scrubs, McGinley has appeared in shows like Burn Notice and Chicago P.D. in recurring roles.

Greg Pitts

In a movie filled with irritating characters, Greg Pitts earns the distinction of playing one of the most annoying: Drew, a friend of Peter's who constantly says crude things about women and drops catchphrases into every conversation in a weak attempt to seem original. Ultimately, Drew is the person responsible for the rift between Joanna and Peter: He tells Peter that Joanna was once involved with Lumbergh, while not bothering to make it clear that the Lumbergh in question is not Peter's odious boss, Bill Lumbergh.

After Office Space, Pitts continued working in small roles on television, including a multi-episode arc as a bullying brother on Grey's Anatomy and as bad boy Tommy White on Sons & Daughters. He also appeared in Judge's Idiocracy in a small role as a cameraman. In recent years, Pitts has picked up small supporting turns on shows like Weeds, Monk, Bones, and The Detour.

Richard Riehle

One of the saddest throughlines in all of Office Space follows Tom Smykowski, played by Richard Riehle, who works as an "engineer liaison" at Initech ... until the Bobs come to town to clean house. Once they figure out that Tom's job is more or less obsolete, Tom gets fired. He subsequently tries to kill himself by running his car in the garage. Thankfully, Tom survives with a new lease on life, helped by a huge settlement that keeps him afloat financially.

If Riehle looks familiar to you, that's not surprising: This veteran actor has racked up a seriously impressive resume over time. Before Office Space, Riehle appeared in films like Fried Green Tomatoes, Fear and Loathing in Las Vegas, The Fugitive, and Lethal Weapon 4. He didn't slow down one bit afterwards, appearing in a plethora of supporting roles in projects like Wedding Crashers, Bridesmaids, A Very Harold & Kumar 3D Christmas, and Transformers: Age of Extinction, among many others. On the small screen, you may have seen Riehle on shows like The West Wing, Grounded for Life (on which he appeared for 45 episodes), ER, Boston Legal, Modern Family, Drunk History, Black-ish, Another Period, and more. Riehle isn't just prolific — he's hilarious in everything he does. Which, given the sheer volume of his filmography, is a seriously impressive feat.

Paul Willson

As the other half of the Bobs, Paul Willson as Bob Porter shows off a peppy exterior that masks the fact that he's there to fire as many employees as he can possibly justify. The Bobs function as one unit, and as McGinley's counterpart, Willson plays his role perfectly. They are in flawless, disgusting harmony, a two-headed hydra of managerial cruelty.

Fans of classic comedy definitely knew Willson long before he showed up at Initech: Well before Office Space, Willson was a fixture on Cheers as Paul Krapence, and on The Larry Sanders Show, where the late comedian endlessly praised Willson's robust improvisation skills. As the years have worn on, Willson has mostly worked on the small screen, appearing on shows like Curb Your Enthusiasm, Malcolm in the Middle, The Newsroom, and The Big Bang Theory. Since 2012, he has also served as the spokesman for Safeco Insurance.

Alexandra Wentworth

As the film opens, Peter isn't just stuck in a dead-end job — he's also trapped in a dysfunctional relationship with Anne, played by Alexandra Wentworth. After forcing Peter to visit a hypnotherapist to deal with his emotional and mental issues — and after the two watch the hypnotherapist die of a heart attack right in front of them — Anne confesses to Peter that she's actually been cheating on him for quite some time, and the two break up immediately.

When Office Space was released, Wentworth — who is usually credited as Ali Wentworth — was already known as a valuable player on In Living Color, and had also appeared as Jerry Seinfeld's girlfriend in Seinfeld's famous "Soup Nazi" episode. After Office Space, Wentworth continued working steadily, appearing in films like It's Complicated and shows like Head Case. In recent years, Wentworth appeared in NBC's revival of Will & Grace and the cult comedy Search Party, and even created her own show, Nightcap, in which she stars as Staci Cole.