China Mieville’s commentary on The Communist Manifesto (it’s called A Specter Haunting) is both very accessible and very “literary” in style, and so might appeal to a book guy (it also has the full text of the Manifesto). It’s obviously not the most theoretically deep text, but that might be a strength and it does a good job contextualizing the original work in a way that’s very fun to read.

Definitely Jakarta Method and Blackshirts and Reds. Possibly a controversial take, but I might go easy on the overly “historical” texts at first. Things like Capital are definitely essential to read, but probably not the best entry point; lots of original Marx is dense, intimidating, and requires a certain amount charitable/sympathetic reading to get beyond the dated language and examples. I’d stick to stuff that either engages mostly with contemporary (or at least latter-20th century) issues OR was written in the last 50 years at first.

If you’re interested in watching movies I’d suggest sitting down and watching with him some old American films like “The North Star”, “Mission to Moscow”, “Reds” (1981). if you’re want something that’s a bit of a surprise, for anyone really, you can sit down and watch with him one of Stalin’s favorite movies called “Circus” (1936).

For more “moderate” and “unbiased”, in the eyes of non-communists, books on Stalin and the period around his life, I’d suggest Red Hamlet: The Life and Ideas of Alexander Bogdanov by James White, Stalin: Passage to Revolution by Ronald Suny, Kotkin’s first book on Stalin, Barbusse’ official biography on Stalin, and anything by Geoffrey Roberts.

For overall learning of the october revolution and the Russian Civil War, John Reed’s “Ten Days That Shook the World”, China Miéville’s “October: The Story of the Russian Revolution”, Leon Trotsky’s “The History of the Russian Revolution”, and Stalin’s “History of the Communist Party of the Soviet Union (Bolsheviks)”

Stalin isn’t generally the greatest luminary in the world, but if you’re interested in the concept of nations, he did write “Marxism and the National Question,” which is a pretty well-received and influential work. I also think “Dialectical and Historical Materialism” and “Foundations of Leninism” are interesting.

Socialism: Utopian and Scientific is, to me, the best way to introduce a fairly-educated person to Marxism.

State and Revolution was very approachable.

Jakarta Method. Definitely. Wretched of the Earth might be a bit much, but it’s a good read that rationalizes violence from the oppressed. Oh, Vijay Prashad’s Washington Bullets pairs great with Jakarta Method.

In my own journey, Zinn (A People’s History) and Lowen (Lies MyTeacher Told Me) were crucial in ripping off the bandaid of American mythology. Still pretty lib though. Advanced levels of that would be Horne’s Counter-revolution of 1776 and Beard’s An economic Interpretation of the US Constitution. I’m sure someone here would also recommend Settlers but I haven’t gotten to it yet. Parenti also has a series of Real History lectures you can find on YouTube.

I can recommend a bunch of books on US political parties as well but idk if you wanna go down that route.

Killing Hope by David Blum for general anti imperialism. Chronological look country by country up to the date of publishing at American interference, coercion or straight up war crimes

I’ve just started reading History as Mystery by Parenti. I’m only on the first chapter but I can already tell it’s an excellent book, and really focused on challenging people’s pre-conceived narratives at their understanding of the world.

Good luck finding a copy though lol apparently there’s only one publishing house in the hemisphere that prints Parenti books, so you’d best look for second hand.

Also recommend

• Anna Louise Strong - The Stalin Era.
• Losurdo - Stalin: History and critique of a black legend.

If he does become interested in historical texts, see my older comment for recommendations

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