Photo by Felipe Bustillo on Unsplash
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Happy Labor Day! I’m a bit late posting because, well, I, too, am taking off this day that on the first Monday of September celebrates the social and economic achievements of American workers.
This federal holiday is rooted in the late nineteenth century, when labor activists pushed for a federal holiday to recognize workers’ many contributions to the growth and prosperity of the United States.
That also happens to be about the time that the film industry was being born.
Long-time readers of the ol’ blog know I am a big movie buff. Film references are sprinkled throughout (or often the main blog peg) for many (many, many) of my posts. My ad hoc tax film critic role even got me a supporting role in a Tax Notes feature on how The IRS Remains the Villain on Screen and Off.
So Labor Day 2026 is a perfect time to revisit some of my favorite movies in which workers played key roles.
I did the same thing on Labor Day 2017 in my post Working, and paying taxes, on holidays. The films cited then, ranging from the Charlie Chaplin silent classic “Modern Times” to Keri Russell’s indie gem “Waitress” to, of course, the wonderful Dolly Parton/Lily Tomlin/Jane Fonda take-down in “9 to 5” of the boss so many of us have hated, still stand almost a decade later as my core perennial job-related movie list.
But, as they say, it’s been a minute. So, dim the lights and start the blog projector for more workplace focused flicks!
Additional worthy workplace movies: With the recent loss of Dolly still hurting, I’ve added a male-centered and darker “9 to 5” comedic take in “Horrible Bosses.” In this 2011 film, lifelong friends Nick (played by Jason Bateman), Dale (Charlie Day), and Kurt (Jason Sudeikis) decide to kill their respective bosses (played to the villainous hilt by Kevin Spacey, Colin Farrell, and Jennifer Aniston) who make each of our protagonists’ cinema lives miserable. Since it’s told from the guys’ point of view, the employers are awful beyond belief. And those of us who’ve had to deal with someone who was as bad, or even just a jerk, can vicariously appreciate their frustrations if not their actions.
Then there’s “Glengarry Glen Ross,” the 1992 version of a group of frustrated real estate salesmen — portrayed by Alan Arkin, Kevin Spacey, Jack Lemmon and Al Pacino, who garnered a supporting actor Oscar nomination for his role — who spend their hours trying to sell real estate to people who don’t really want to buy. The pressure is on because the home office, represented in a brief but scathing appearance by Alec Baldwin, is holding a sales contest.
Yeah, I’m seeing the bleaker trend of my workplace movie choices this year. But this still is a great film, and one also featured in my “The Money Message in Movies” piece I created many years ago.
But let’s change reels and pivot to a bit lighter film fare.
Happier places to work, or at least watch: As a person of a certain age who is transitioning into reduced work, the 2015 movie “The Intern” resonates a bit more now. Robert De Niro plays Ben, a man looking for something to relieve retirement boredom. He finds it as an intern at a startup helmed by Anne Hathaway’s Jules. Yes, predictable, so the following is not a spoiler. By the movie’s end, the duo overcome initial reservations about each other and help each grow as workers and people. Good for them. I don’t think, though, I’m going to want to transition back into the workforce once I finally fully leave it!
Another Hathaway workplace comedy is the original “The Devil Wears Prada.” In the 2006 movie, she’s the idealistic recent college graduate who is a junior assistant to Meryl Streep’s tyrannical high-fashion magazine editor. Again, spunky worker survives demanding/abusive boss to prove her worth and learn important life lessons. But the real star is, of course, Streep. And they should have just left it there, as the 2026 sequel, despite the wonderful cast’s reunion, sags.
Animated workplaces: And, of course, there are some ostensible children’s movies. But just because they are animated doesn’t mean that they aren’t also for adults. Two such features join my 2026 additions to the worthy workplace movies list.
In “Bee Movie” from 2007, Jerry Seinfeld voices Barry B. Benson, a bee who has just graduated from college. Unhappy with his lone career choice of making honey, he opts instead to make the ultimate American move: he sues humans for stealing the bee’s honey.
Then there is “Monsters Inc.” As befitting a Disney production, this 2001 animated spectacle celebrates the support we all rely on from our coworkers. That especially critical when pals Mike (voiced by Billy Crystal) and Sulley (John Goodman) accidentally unleash a child onto Monstropolis and uncover a giant conspiracy that goes all the way to the top of Monsters Inc. Drama! Animation! Best Friends! What more can you want?
Mount Workmore honorees: Finally, I want to share the X (still Twitter to me) post below from Chicago film critic Richard Roeper citing his selections for moviedom’s Mount Workmore.
He gives us four great choices, and I’m not biased at all that two on my 2017 list — “Office Space” and “9 to 5” — made Roeper’s film monument.
But I had to comment on his post to add another of my all-time worker movie favorites that is perfect for Labor Day, “Norma Rae.”
Since this holiday originated when labor activists pushed for a federal holiday, a movie celebration unionization successes has to be mentioned. And I’ve mentioned “Norma Rae” several times in the ol’ blog.
Back on Labor Day 2015 I offered the tax tip that Union dues might be tax deductible. A key scene from the 1979 movie, for which Sally Field won her first Oscar as the titular character, is featured in the post.
Then Sally as Norma Rae got another citation in my Labor Day 2018 post when the union dues tax deduction was axed by the Tax Cuts and Jobs Act of 2017.
So, with that tax law linkage, we roll the final credits on this sequel to my favorite films that in some way are connection to work.
You can find most of these on the gazillion streaming services out there, or available to rent or buy. Enjoy one or more today, or any time you don’t have to be at work.
