Thanks for dragging me in and bumping the thread. I've been meaning to dig into it.
I can't really speak for what influenced me in a liberty direction when I was very young, because in all honesty, when I emerged from the public school system and even a couple years into college I was a fully indoctrinated egalitarian progressive. Seeing the Gary Cooper Fountainhead movie in my late teens was my gateway to any kind of liberty thinking and sent me on a sharp 180.
Now, having read to my kids for 16 years, I'm sure I could pick out some liberty-friendly literature, and I'll try to beat my brain a little bit in the next few days.
My kids have all been homeschooled. My wife directs a TJEd-based commonwealth school. The older kids are involved in "scholar projects" involving founding American documents that have gone very in-depth. It may seem a bit of a gimmick, but my 13 & 16 year olds can recite the Declaration from memory. They are doing other literature projects as part of their projects there. My oldest twins just finished the Count of Monte Christo to be ready for discussion this week. TJEd was developed by LDS folk so materials tend to be filtered through that lens.
The commonwealth school also puts on plays. My older kids (16 yo twins and a 13 yo) have each read 15-20 Shakespeare plays and have performed in A Midsummer Night's Dream. They have substantial roles in As You Like It next month.
Although I think art with a clear individualist/liberty message is mandatory, I'm not a big believer in limiting the kids to liberty-indoctrinating material. I'm an arts guy, and there's tons of life-enriching, profoundly significant stuff written, composed, sculpted, painted, danced, etc. by pinko commies. In fact, collectivists/socialists have tended to be far better artists in terms of craftsmanship, originality, creativity and even plain capitalistic commercial success than limited governement individualists. I don't see this changing anytime soon. This will horrify some here, but my older kids have caught onto the Hamilton craze and can recite every word (including the bad ones). I'm NOT a fan, but it's amazing how deep our conversations about government can go when they have the context of the founding documents they've been studying combined with the left-wing hip-hop musical take on it. I also don't follow the R-rated movie guideline very consistently. My wife and I and our 16-year old twins had a great viewing of The Shawshank Redemption a few months ago.
Right now, my 6-year old is really into The Magic Treehouse series. I wouldn't necessarily recommend it as great literature, but I suppose it could encourage independent thinking and a thirst for knowledge. They're okay if you don't consider the books for more than they are, and take them as adventure stories where the kids use book knowledge to navigate through the worlds they end up in.
As a family reading in the evening we've been through Tom Sawyer, Huckleberry Finn, Charlie & the Chocolate Factory, Wind in the Willows, Peter Pan, Alice In Wonderland/Through the Looking Glass, The Hobbit, the 1st three Harry Potter books, The Wizard of Oz, a little of Heinlein's juvenile writing and probably lots more I can't remember. My wife has done tons of others with them in the course of homeschooling, which hasn't stuck to any particular curriculum but is probably closest to Charlotte Mason/Ambleside, very literature-based.
Although it can't be avoided, I dislike anthropomorphic animal stories (perhaps Watership Down excepted). I've made no bones about it with my kids. As a result, my daughter has rebelled and started making elaborate fur suits. But she's good at it and wants to do business selling her wares, so I guess I'll give it a pass.
I second the recommendation for the Tuttle Twins books. I read the Miraculous Pencil with my 6 & 13 year olds last week. What a fantastic message to cure ANYBODY of the misguided idea that trade and labor protectionism could be beneficial to society.
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