Well this is where I differ from many other libertarians. I’m for natural order. If a given society frowns on price-gouging, for example, and they understand the economic hit they are taking because of their rejection of price-gouging (they just find it that offensive), I don’t have anything to criticize about that. If a show painted price-gouging in a bad light, I’d lament the economic ignorance but I wouldn’t be disgusted by the morality like perhaps many libertarians would.
SM:
I look at Seinfeld (my favorite tv comedy of all time) kind of the same way I look at Sartre’s books. It’s a lot of leftist hoo-ha, but it’s so damn accurate and honest about the failings of that particular subset of people. Larry David is completely unflinching in eviscerating his own kind. Even when they are somewhat making fun of the other (like the episode in Curb where they try to join the Waspy-Republican country club) the humor comes more from them trying to pretend to be what they think the stereotype of a Rockefeller Republican is.
Edit: this is probably why something that is pure “true believer” entertainment kind of sucks, even if it’s full on pro anarcho-capitalist… because anything that portrays the chosen people group as so enlightened and infallible is an insult to one’s intelligence and just plain inaccurate
I can’t believe no one has mentioned Sopranos! That has gotta be the greatest thing on tv, ever. Constantly showing the connection between govt and mafia, incredibly entertaining, and just thought-provoking enough to keep out the assholes.
Larry David’s concern with social conventions is really interesting to me. Both Seinfeld and Curb are great at making people think about undesigned and voluntarily practiced customs.
But some obvious shows for libertarians:
Homeland (helmed by the creators of 24, but much, much more ambiguous than that show)
Firefly, and its feature film Serenity (Whedon’s next show, Dollhouse, was also big on individualism, contracts, corporatism, etc.; can’t speak for his previous shows, Buffy and Angel)
Deadwood (order emerging from the bottom up)
The Wire (unintentional dramatization of public choice critique)
Yes, Minister and Yes, Prime Minister (intentional dramatization of public choice; the co-creator said “public choice economics… was at the root of almost every episode”)
The Thick of It and Veep
But I’m more interested in what the great comedians like Hicks are thinking. That’s the thing, it’s not just rote repetition of dogmas. And Hicks’s social insights are nothing short of penetrating. I don’t like his misanthropy and I think that libertinism is generally erosive to healthy social order but that’s beside the point. If you listen carefully to what he says, you realize that he’s actually thought about what he’s saying and that he’s bringing something more to the table in terms of relevancy and holistic social criticism than can be found in academic libertarian thought. And it’s always difficult to know when a satirist is merely satirizing and when he’s verbalizing his own heartfelt sentiments. That’s what sets a great satirist apart from all the rest.
Again, I think that Carlin is just too complex to be labeled. And I would be careful about simply concluding “well, he mentioned Social Security in a positive light, so he must believe in the New Deal and be a socialist”. His message was tailored to his audience - he even said as much - and the audience generally doesn’t understand that there’s something wrong with Social Security. To them, it is synonymous with “taking care of old people.”
All I can say is that his insights into human nature are penetrating. What I like about all these guys is that you can tell they are speaking from the heart, that is, they aren’t just repeating something they learned in ECON 101 or read in a textbook or heard from a bleeding-heart sociology professor. They might be misguided on this or that, but there’s something really going on upstairs which, to me, is the most important thing.
Clayton -
I watch NCIS
Its pretty statist but i like their character development and mysteries. Been watching it for years.
Chris Rock had two great bits on taxes:
Watch the comedy show “Parks and Recreation”! A character in that show, Ron Swanson, is a full blown libertarian anarchist, as well as a rugged individualist type. And the rest of the show is hilarious as well, I think.
"The Wire (unintentional dramatization of public choice critique)"
OMG that is so true.
I’m not really bothered by statist leanings in my TV shows. I actually prefer them to be as apolitical as possible - usually when I sit down to watch TV I just want to relax and not think about morals and whatnot. But there are two shows I’m suprised have not been mentioned so far, which in my mind are as libertarian as they get:
Penn & Teller’s Bullshit
South Park
Yes, it is an anime, one of the betters ones in my opinion. At its core its a simple love story that relies on the interaction between the two lovers teasing one another. Its the setting that interests me personally though. They live in feudal Europe and the man is a travelling merchant. The story arcs revolve around him doing ordinary business. The antagonist? The monolithic state.
One of the arcs for example has the state trying to create fiat currency by stamping authorized gold with their mark. Any gold that doesn’t have the mark can’t be used as currency and can’t enter the town. What do the pair do? They smuggle it in and make a tidy profit.
Another arc has a speculative bubble occuring. The pair destroys it by dumping a massive supply of the otherwise useless rock everyone wants.
Well I also watch Samurai Champloo (an anime) and Curb Your Enthusiasm. I really, really, really want to see more of The Sopranos, but alas, I have only seen the pilot episode, and HBO makes all of their DVDs too damn expensive. And I keep on telling Neodoxy to see Samurai Champloo, but he never listens like the dumb Peace and Freedom Party militant that he is.
How about Trigun, talk about an NAP-respecting character 
Vash may respect NAP when it comes to human lives, but he certainly has no problem destroying property.
There really is something great about an insurance company being the one trying to stop his hijinks though.
Lol, so true, forgot about that 
Right now I’m slowly attempting to put together a machinima series about an Austrian economist. I’ve shelved all of my film projects for the time being though, being that I’ve just sent off a short story to the New Yorker and I’m working on another one while I wait for a response that I plan on sending to Zoetrope: All-Story.
I’ll just leave this here…
“And I keep on telling Neodoxy to see Samurai Champloo, but he never listens”
Look, it’s on my to do list okay? I’m a very busy little militant! I’ve got a lot of shows that I need to watch, and that’s not even including the various anime people have recommended to me
Also, what pro-libertarian themes do you see in breaking bad? I see that it has some themes which could be interpreted as individualistic, if not libertarian, but all and all I would see it as being neutral in regards to statism.
I see it as being extremely anti-drug prohibition, and every time there’s an encounter with the law, the law is almost always portrayed in a negative way (Walter getting maced, boisterous old Hank, etc.)
And it’s on the fucking internet! How damn hard can it be to watch!?
EDIT
Plus there’s Gale, who is portrayed as a very intelligent man, who is a staunch libertarian. (We see a Ron Paul sticker in his notes later on.)
Meh, but at the same time I don’t really see that as one of the central focuses of the show. the negativity of drug prohibition can be inferred, but then again it also shows the kind of people who both buy and sell this stuff, and the picture painted is not pretty. Also I partially agree that the police are shown in a negative light, mainly through hank (the living embodiment of everything that I hate in the human race) but at the same time they are never given an extremely harsh examination. When Walter gets maced he’s being an ass to a cop who’s kind of just trying to do his job and do it fairly. Gale also looks like a fool who gets way in over his head (which, in a way, he certainly does).
And it’s time, not being able to find the show!
Is literature allowed? Read all the Garet Garrett novels. Especially The Driver.
Also, look at your avatar. Watch every movie staring that man (although you probably already have).
Then take out Clint Eastwood for a spin and watch the Dollar trilogy.
Then watch Desert Punk, yet another underrated anime.
Basically, if it’s noir, it’s golden. If it’s neo-noir, it’s golden. If it’s anything punk, it’s o.k.. If it’s anything cyberpunk, it’s better. And if it’s cypherpunk, then it’s hands-down 5-stars.
(tl;dr, look out for the movies in the intersection of good punk/cult and what the mainstream hate)