3 Best Movies to Watch This Labor Day

Published Sep 7, 2026, 5:43 AM EDT Simon Gallagher has worked in movie and TV journalism for more than 17 years. He has written more than 6000 articles and reviews, and edited thousands more. He is an expert in the entertainment industry, particularly in the golden age of screen superheroes. Simon is also a Rotten Tomatoes approved critic. Given how much of our lives we spend dedicated to it, it’s no real surprise that work culture forms the backbone of a huge number of major movies. Even cinematic icons like Indiana Jones have day jobs and quite possibly suffered the same existential Sunday night dread that greets non-swashbuckling hero types. And the spectrum of how movies handle the workplace is also massive. There are infectious commentaries on so-called McJobs like Ryan Reynolds’ Waiting... or indie darling Clerks, where low-paid malcontents survive by weaponizing cynicism behind a counter and the customer is invariably always wrong. And at the other end of the scale, Hollywood also does a good line in all-too-real, morally bankrupt fantasies like The Wolf of Wall Street or Boiler Room. And somewhere in the middle there are gentle meditations on existence like Up in the Air or The Holdovers, gentle rom-coms like Waitress, and even psychotic nightmares like American Psycho. All are in some way dependent on the work at their hearts and how they define their characters. Labor Day is, of course, designed to honor the American worker, and what more cathartic a way to celebrate the long holiday weekend than by watching people struggle through and revolt against the American workplace? It’ll almost certainly make you feel better about having the time off and going back to somewhere far better than anything depicted in these masterpieces. If you are looking to spend your time off indulging in some top-tier workplace cinema, these three picks have got you covered. 3 Office Space (1999) Mike Judge’s cult comedy classic Office Space perfectly captures the very specific late-’90s purgatory so ubiquitous that it was also the mundane reality Keanu Reeves’ Neo fought against in The Matrix. It’s a quiet scream against office mundanity, passive-aggressive middle management violence, and it ends up as a satirical working-class fantasy whose dream is simple: apathetic non-compliance that turns into all-out warfare. Office Space is hugely quotable, and there are some truly excellent moments, like the cathartic revenge taken on a printer - a surely near-universal fantasy for anyone who has ever used one - but the real magic is in the character chemistry, led by Ron Livingston’s hollowed-out Peter, who is unwittingly freed from his nightmare by an incomplete hypnotherapy session. The rest of the cast includes the always-excellent Stephen Root, Jennifer Aniston at the height of her Friends fame, John C McGinley, and a masterclass performance from Gary Cole as Bill Lumbergh, the poster boy for passive-aggressive micromanagement. Chillingly, his cartoonish corporate speak nonsense seems to have become the perverse blueprint that an entire generation of LinkedIn power users now unironically uses. It might soon strange, but Fight Club shares some DNA with Office Space, even if its solution to the Narrator's beige corporate purgatory is rather more extreme. 2 9 to 5 (1980) This year, more than ever, there’s good reason to rewatch Dolly Parton’s 9 to 5 after the legendary singer, actor, and philanthropist sadly died. She was already a huge musical star by 1980, of course, but when Jane Fonda was inspired to cast her as Doralee Rhodes, one of the three leads in an idea inspired by real-life Boston organization "Nine to Five". But even without that tragic reason, 9 to 5 is a wonderful workplace comedy that again sits alongside Office Space as a cathartic working class tale of revenge against a toxic work environment. There’s also a similar sort of office camaraderie as Parton’s Doralee, Fonda’s Judy, and Lily Tomlin’s Violet are united in their disgust at the management of despicable Vice President Franklin Hart Jr. (a delightfully loathsome Dabney Coleman). 9 to 5 is an old-fashioned, charming comedy of errors that slips from farce into moments of surprising darkness, and again, the pleasure is all in the empowerment of the three women taking back their agency. 1 Glengarry Glen Ross (1992) Office Space and 9 to 5 are presented as fairy tales of empowerment that both triumph over toxicity, but Glengarry Glen Ross is a completely different animal. The legendarily well-written thriller is a bit like having a panic attack for 100 spell-binding minutes as David Mamet bludgeons you repeatedly over the head while screaming curse words at you. Somehow, it’s still remarkably entertaining, despite being about a real estate agency. Based on Mamet’s own stage play, the profanity-riddled movie is populated with a quite remarkable cast, led by Jack Lemmon as the tragic Shelly “The Machine” Levene, Al Pacino, Ed Harris, Alec Baldwin, Kevin Spacey, and Alan Arkin. “Powerhouse” doesn’t even seem to cover it. You really shouldn’t be as invested, nor as compelled by a competition to close the most property sales, but it’s such a masterclass of acting and scriptwriting that that doesn’t even register. Office Space Release Date February 19, 1999 Runtime 89 minutes 9 to 5 Release Date December 19, 1980 Runtime 109 Minutes Director Colin Higgins Writers Patricia Resnick, Colin Higgins