It's not Avatar (2009) nor Wall Street (1987) nor even Salt of the Earth (1954) a film which was banned for alleged "communist propaganda."
After reading too many film analyses from philosopher Slavjo Zizek, I've come to the conclusion that what can arguably be called the most progressive movie in the last half century or so is the 1999 film Office Space. On its surface, the film looks like a simple satire of life as a white collar software worker but underneath lies something much more revolutionary.
The film centers around Peter Gibbons (Ron Livingston) who is alienated with his job at Initech. What's interesting is Gibbens doesn't hate his job for a lack of pay-which he receives well and lives in modest comfort-it's the lack of dignity with his work. At one point saying, "Now if I work my ass off and Initech ships a few extra units, I don't see another dime, so where's the motivation?" In the same scene we he see that Peter answers to eight bosses, as he points out
...So that means that when I make a mistake, I have eight different people coming by to tell me about it. That's my only real motivation is not to be hassled, that and the fear of losing my job. But you know, Bob, that will only make someone work just hard enough not to get fired.
Notice this transcends Marxist notions of capitalism as exploitative and takes on a
left libertarian-that is to say, anarchist-critique of the system as one controlled by domination and fear. In the book
Redemption and Utopia, chronicling libertarian thought throught Europe, a similar case is made for Franz Kafka who in his political writings "[l]ays a typically anarchist stress on the oppressive and authoritarian nature of the existing regime (and on economic exploitation as does Marxism)."
It's no wonder that in the film, bosses and managers are portrayed as the very psychological definition of authoritarian. The psychologist Bob Altemeyer in his book, The Authoritarians lays out the profile and results of numerous personality tests and surveys of what defines authoritarianism. He notes that while these people appear as "nice, ordinary people" they have a deep love and respect for authority and hatred for anyone that goes against it. One of the defining characteristics is "avoid[ing] anything approaching a fair fight...It’s striking how often authoritarian aggression happens in dark and cowardly ways, in the dark, by cowards who later will do everything they possibly can to avoid responsibility for what they did."
In the film this is epitomized by the corporate manager Bill Lumbergh (Gary Cole) who like the other managers, will fire people behind their back. Later in the film when Peter surpasses Lumbergh on the corporate food chain, he unquestionably accepts Peter's reckless behavior. When Peter takes out a wall in his cubicle clearly obstructing people on the floor, Lumbergh can only reply with a dry "Uh...we'll go ahead and, uh, get this all fixed up for you later."
As the story goes, Peter goes to a therapist after his disenchantment, and in a botched hypnosis goes into a happy trance state. Within those days, his odd attitude convinces the managers that he is in highly competent when really he is semi-delusional. In what seems to be a satire of the "Peter Principle" is in fact something greater. It is a clear demonstration that one has to accept a rigid ideology, delusionally even, to succeed in the corporate world.
However this wears off after learning that his friends, Michael and Samir, are about to fired and the team embarks on a way to get even. In their act of retaliation, they plan a hacking scheme in which a computer virus steals fractions of transactions and puts them into an account, which, given enough time, would amount to six figures if not higher.
While on a surface a simple criminal scheme of revenge, is it not a way to get back the lost fruits of their labor? As Peters tells Michael, "For five years now, you've worked your ass off at Initech,...Five years of your mid-20s now, gone. And you're gonna go in tomorrow and they're gonna throw you out into the street. You know why? So Bill Lumbergh's stock will go up a quarter of a point."
Once the plan goes awry, Peter submits the lost money with an apology knowing it will indict him. However, in a solution to the whole ordeal, the worker Milton burns down the office eliminating the evidence of all wrongdoing. Done in an obviously comedic manner, it follows a truly revolutionary (in the sense of activism) logic: the only way out is to burn it all down.
In fact, by comparison almost no film holds up. In similar movies like Tower Heist (2011), the characters are justified because the antagonist uses criminal means to get his way, here, what the company does isn't just legal, it's downright mundane. In fact, even Salt of the Earth a film that was outright blacklisted, looks downright bougie. In the film, a union of mine workers go on strike and eventually win better working conditions. In Office Space, a group of workers try to steal from the company and one burns it down.
And for those that still think I'm looking too far into this, that it's just a comedy movie, even the director Mike Judge's other works suggests are rather pro-worker leaning.
Judge, who also created King of the Hill has an episode where the blue collar propane salesman Hank allies with hippies in running a self-managed cooperative that is eventually bought out and ruined by a large corporation. Notice here, despite the cultural split, they are joined by a love and appreciation for labor, with self-managed work as the apex of quality and freedom.
I don't think anything even comes close to approaching that.