So here are my choices, in alphabetical order…
1776 (1972)
What could be more libertarian than a movie about the writing of the most eloquent argument for liberty in history, the document that declared “all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness”? A rousing Broadway musical effectively transferred to the screen, showing the real men who debated, argued, nitpicked, and stormed out during the spring and summer of 1776.
John Adams: A second flood, a simple famine, plagues of locusts everywhere, or a cataclysmic earthquake, I’d accept with some despair. But no, You sent us Congress! Good God, Sir, was that fair?
Amazing Grace (2007)
John Newton was a slave trader who was converted to Christianity. He renounced his previous life and became an evangelical minister in the Church of England, an abolitionist, and the author of a beautiful hymn. “Was blind but now I see,” indeed. Among the people who heard his preaching was a young member of parliament, William Wilberforce, who was inspired to lead a long campaign for the abolition of slavery—from his maiden speech in 1789 to the final passage of the Abolition Act a month after his death in 1833. This movie reminds us that humanity has made great progress toward freedom, that each battle for freedom can be long and seemingly futile, but that the goal is worth time and money and effort.
Charles James Fox: When people speak of great men, they think of men like Napoleon—men of violence. Rarely do they think of peaceful men. But contrast the reception they will receive when they return home from their battles. Napoleon will arrive in pomp and in power, a man who’s achieved the very summit of earthly ambition. And yet his dreams will be haunted by the oppressions of war. William Wilberforce, however, will return to his family, lay his head on his pillow and remember: the slave trade is no more.
Amistad (1997)
This movie tells a fascinating story about a ship full of Africans who turned up in New England in 1839. The question: Under American law, are they slaves? A long legal battle ensues, going up to the Supreme Court. People often quote the Shakespeare line, “The first thing we do, let’s kill all the lawyers”—not realizing that that line was said by a killer who understood that the law stands in the way of would-be tyrants. Amistad gives us a picture of a society governed by law; even the vile institution of slavery could run up against the rule of law. And when the former president, John Quincy Adams, makes his argument before the Supreme Court, it should inspire us all to appreciate the law that protects our freedom.
John Quincy Adams: If the South is right, what are we to do with that embarrassing, annoying document, The Declaration of Independence? What of its conceits? ‘All men created equal,’ ‘inalienable rights,’ ‘life, liberty,’ and so on and so forth?
Dallas Buyers Club (2013)
This movie has a strong libertarian message about self-help, entrepreneurship, overbearing and even lethal regulation, and social tolerance. A homophobic working-class Texan learns in 1985 that he has AIDS and is given only 30 days to live. Unwilling to accept that prognosis, he goes looking for drugs, finds them in Mexico, and starts selling them in Texas, mostly to gay men. The FDA is not happy that people with terminal illnesses are making their own decisions. You’ll be surprised to see how many armed FDA agents it takes to raid a storefront clinic operated by two dying men.
Dr. Eve Saks: None of those drugs have been approved by the FDA.
Ron Woodroof: Screw the FDA. I’m going to be DOA.
East-West (1999)
Films about the devastation of communism are all too rare. This French film (Est-Ouest) about Soviet emigres who returned to Russia after World War II is a lush and moving depiction of, as the New York Times put it, “the grim reality of life and death in a police state”: poverty, executions, and constant fear. The movie shows the desperation of one returning family, and their hope that a family friend played by Catherine Deneuve can help them get out again.
The Man in the White Suit (1951)
A shy scientist played by Alec Guinness invents a cloth that will never wear out and won’t get dirty. What an amazing contribution to human wellbeing! A British textile mill sets out to produce it. But then the other mill owners, and the unions, realize that its production would mean that people won’t need to buy many clothes. When the unions confront the owners, one assures them there’s no conflict: “Capital and labor are hand in hand in this.” They join forces to protect their positions and block progress. A metaphor for so much of political activity aimed at stopping innovation, creative destruction, and improved living conditions.
Daphne: Don’t you realize what this means? Millions of people all over the world are living lives of drudgery, fighting an endless losing battle against shabbiness and dirt. You’ve won that battle for them. You’ve set them free. The whole world’s going to bless you.
My Beautiful Laundrette (1985)
This is something of a ringer on a libertarian list. The novelist/screenwriter Hanif Kureishi thought he was making a savage indictment of Thatcherite capitalism. But to me, the good characters in the movie—white and Pakistani, gay and straight—are the ones who work for a living, and the bad characters are clearly the layabout socialist immigrant intellectual, who doesn’t like his son opening a small business, and the British thugs who try to intimidate the young Pakistani businessman. My favorite line: The enterprising brother of the whining intellectual takes a young working-class Briton with him to evict some deadbeat tenants. The young Brit suggests that it’s surprising the Pakistani businessman would be evicting people of color. And the businessman says, “I’m a professional businessman, not a professional Pakistani. There is no question of race in the new enterprise culture.” I think Kureishi thinks that’s a bad attitude. The joke’s on him.
Pacific Heights (1990)
This one is a thriller that is almost a documentary on the horrors of landlord-tenant law. A young couple buys a big house in San Francisco and rents an apartment to a young man. He never pays them, and they can’t get him out, and then things get really scary. The lawyer lectures the couple—and the audience—on how “of course you’re right, but you’ll never win.” I just knew this happened to someone—maybe the screenwriter or someone he knew. Sure enough, when Cato published William Tucker’s book Rent Control, Zoning, and Affordable Housing, and I asked Pacific Heights director John Schlesinger for a jacket blurb, he readily agreed to say “If you thought Pacific Heights was fiction, you need to read this book”; and he told me that indeed the screenwriter had gone through a tenant nightmare.
The Palermo Connection (1990)
Here is an odd Italian-made movie (but in English) cowritten by Gore Vidal. New York city councilman Jim Belushi runs for mayor on a platform to legalize drugs and take the profits out of the drug trade. The Mafia isn’t happy. His life is threatened. So he decides to go on a honeymoon, in the middle of his campaign—to Sicily—where he encounters more men prepared to stop him by any means necessary. How did the New York Times not review this movie?
Shenandoah (1965)
Some have called it the best libertarian film Hollywood ever made. James Stewart is a Virginia farmer who wants to stay out of the Civil War. Not our fight, he tells his sons. He refuses to let the state take his sons, or his horses, for war. Inevitably, though, his family is drawn into the war raging around them, with tragic results. I cried when I was 11 years old, and I teared up again when I heard the Stewart character sing the antiwar ballad “I’ve Heard It All Before” in a musical version. This is a powerful movie about independence, self-reliance, individualism, and the horrors of war.
Boy: What’s confiscate mean, Pa?
Charlie Anderson: Steal.
No two libertarians are going to have the same list.
Miss Liberty’s Film and Documentary World offers a somewhat different Top 25 here. Libertarians might also find helpful this warning from the Guardian: “The Giver, Divergent and the Hunger Games trilogy are, whether intentionally or not, substantial attacks on many of the foundational projects and aims of the left: big government, the welfare state, progress, social planning and equality.”
Leaving aside the tenuous claim that big government, the welfare state, and social planning lead to progress and equality—see, for instance, East-West—it sounds like those just might belong on a libertarian list.