For our annual summer countdown, we are looking at our favorite 25 movies that were not huge hits during their initial release, but mean a lot to us. Check out last year’s Summer of Stars countdown or the year before when we did blockbusters! Find the rest of the Flop and Fizzle series here!

by Fiona Underhill, Contributor

From 1996-2003, the actor Ron Livingston appeared in four important cultural touchstones for me: Swingers (1996), Office Space (1999), Band of Brothers (2001) and Sex and the City (2002-2003). In the last of these, he made an impression as one of Carrie’s worst boyfriends, infamouly breaking up with her via Post-It. Using a standard office supply to strike such a wounding blow to the heart is particularly ironic, given the office attitudes of what is probably his most iconic character to date–Peter Gibbons. 

Mike Judge is best-known for creating Beavis and Butthead and King of the Hill, but he also wrote and directed one of the best workplace comedies of all time. Even before the UK series The Office was aired–inspiring the ultra-successful American version–there was Office Space. The film centers around Peter Gibbons, a young man who absolutely hates his cubicle office job: “Every day that you see me–that’s the worst day of my life.” 

Peter’s work besties are the affable Samir Nagheenanajar (Ajay Naidu) and Michael Bolton (David Herman), a white dude who absolutely loves gangster rap and absolutely hates his namesake. Fun fact: Michael calling the singer a “no-talent ass-clown” is the first use of now popular clown-based insult. Michael’s love of gangster rap provides the film with a hilariously incongruous but brilliant soundtrack, comprised of tracks such as Geto Boys’ “Still” and “Damn it Feels Good to be a Gangster” and Ice Cube’s “Down for Whatever.”

The trio bond over their shared nemesis, the printer: “PC load letter? What the f--k does that mean?!” The scene where they do a Mafia-style execution on the printer in a field with baseball bats has been much-replicated since. Gibbons also despises his boss Bill Lumbergh (Gary Cole) and his repeated catchphrases of “What’s happening (rhetorical)” and “I’m gonna have to go ahead and ask you to….” Many things push Gibbons over the edge and close to absolutely losing it – not least when a colleague says, “Sounds like someone’s got a case of the Mondays.”

One of the many shining stars in the over-all brilliant ensemble is Stephen Root as Milton, the character who initially inspired the film. Milton’s love of his beloved Swingline stapler and his insistence on receiving a piece of birthday cake being passed around the office leads him to mumble, “I’ll set the building on fire”–something that no one hears or takes seriously. Office Space is a film that my husband and I bonded over early in our relationship, and to this day, the most romantic gift I’ve ever received from him is my very own Swingline. John C. McGinley and Paul Wilson as The Bobs–consultants brought in to appraise the workers and downsize accordingly–also make for some memorable lines and scenes.

Outside of the office, there’s Diedrich Bader as Peter’s neighbor Lawrence, who talks to him through the thin walls in their crappy apartment complex. Jennifer Aniston gets one of her best-ever movie roles as Joanna, a waitress railing against the many ‘pieces of flair’ she’s forced to wear at a restaurant that definitely isn’t TGI Fridays. 

Office Space has come to the public’s attention more in the last year, thanks to the critically-acclaimed TV series Severance. Gibbons visits a hypnotherapist (Mike McShane) and asks him, “Is there any way that you could sort of zonk me out, so I don’t know that I’m at work in here (in my mind)? Could I come home and think that I’ve been fishing all day or something?” This became the basic premise of Severance.

Office Space is a perfect encapsulation of Y2K panic and represents one of the last gasps of Gen-X 90s ennui before 9/11 changed everything. The trio’s nefarious Superman III plan is predicated on Peter’s task to get the office ready for the millennium, an actual job that my Stepdad had in the late 90s too. The film has become a bastion and rallying cry for bored and frustrated office workers everywhere, and it could certainly be used as an argument against returning to the office after the first few years of the global pandemic.

While Office Space is certainly a product of a now bygone era, the dialogue is still endlessly quotable (and gets referenced at least weekly in our house), and it holds up to revisits. The movie was not a success when it was first released, as the studio had no idea how to market it, but has gone on to become a cult hit via home release. It’s one of the best comedy movies of the 90s and absolutely doesn’t deserve to be called a flop, as the whip-smart dialogue and pitch-perfect performances endure to this day.