Cast of Office Space The Ultimate Guide: 1 Minute to Discover the Key Players Behind the Cult ClassicSarah ThompsonSep 08, 2025Table of ContentsMain Cast MembersNotable Supporting CastTips 1:FAQTable of ContentsMain Cast MembersNotable Supporting CastTips 1FAQFree Smart Home PlannerAI-Powered smart home design software 2025Home Design for Free"Office Space," released in 1999, is an iconic workplace comedy film directed by Mike Judge. It has achieved cult status thanks to its satirical portrayal of corporate culture, memorable characters, and relatable storyline. If you’re curious about the talented actors who brought these characters to life, here’s the ultimate guide to the main and supporting cast of "Office Space."Main Cast MembersRon Livingston as Peter Gibbons: The film's protagonist, Peter is an unfulfilled software engineer who rebels against his mundane, soul-crushing corporate job.Jennifer Aniston as Joanna: Peter’s love interest, a waitress at Chotchkie's who’s equally frustrated with her working environment.Gary Cole as Bill Lumbergh: The iconic, overly bureaucratic boss at Initech, recognizable for his monotonous voice and obsession with TPS reports.David Herman as Michael Bolton: Peter’s friend and co-worker who detests both his job and sharing his name with the famous singer.Ajay Naidu as Samir Nagheenanajar: Another of Peter's colleagues, Samir is regularly frustrated by people mispronouncing his last name.Stephen Root as Milton Waddams: A meek employee with a penchant for his red stapler, Milton is frequently bullied and overlooked in the office.Diedrich Bader as Lawrence: Peter’s laid-back neighbor who offers comic relief and alternative perspectives on life's problems.Notable Supporting CastJohn C. McGinley as Bob Slydell: One of the two efficiency consultants ("the Bobs") brought in to streamline the company.Paul Willson as Bob Porter: The other "Bob," focused on analyzing which workers should be fired.Richard Riehle as Tom Smykowski: An eccentric employee whose invention ideas play a memorable part in the story.Alexandra Wentworth as Anne: Peter’s girlfriend at the outset of the film.Greg Pitts as Drew: Peter’s annoying co-worker, famous for his “O-face.”Orlando Jones as Magazine Salesman: Delivers a classic cameo scene, posing as a questionable magazine salesman."Office Space" stands out not only because of its clever script and direction but also thanks to its perfectly cast ensemble. As a designer, I often notice how every character's environment—be it the dull office cubicle or the eclectic diner—reflects their personalities and stories. This is why exploring the office layout planner can be so helpful for anyone inspired to recreate that iconic Initech vibe at home or in a modern workplace setting.Tips 1:If you’re inspired by the film’s depiction of corporate spaces, pay attention to how set design and scene layout influence the mood and story. When designing your own office, consider optimizing not just for productivity but for well-being—think about lighting, color, and the arrangement of personal workspaces. Tools that let you visualize different layouts in 3D can help you break out of the drab "cubicle farm" look and create an environment people actually enjoy.FAQQ: Who played Michael Bolton in “Office Space”? A: Michael Bolton was portrayed by David Herman.Q: What is the name of the irritating boss in “Office Space”? A: The boss is Bill Lumbergh, played by Gary Cole.Q: Was Jennifer Aniston a main character in “Office Space”? A: Yes, Jennifer Aniston played Joanna, Peter Gibbons’ love interest.Q: Who played Milton and why is his character memorable? A: Milton was played by Stephen Root. He’s memorable for his obsession with his red stapler and his mumbling frustrations.Q: Is “Office Space” based on any previous work? A: Yes, it was inspired by Mike Judge’s animated shorts featuring the character Milton Waddams.Home Design for FreePlease check with customer service before testing new feature.