What works of art/literature best address the following polical/policy questions?

Seconded a thousand times.

Callahan’s Law: “Shared pain is lessened; shared joy, increased—thus do we refute entropy.”

Ursula K. LeGuin’s book “The Dispossessed” had a lot to say about capitalism and socialism.

Heinlein’s “Starship Troopers” has a lot to say about how governments manipulate people … much more subtly and intelligently described than in the movie based on the book, and I thought the movie was pretty good.

“Weapon Shops of Isher” deals with the limits of government control.