That's all. Maybe I didn't read that stuff you read.
He's been writing since the 1970s with National Lampoon. He became political midway through his career. He started as a libertarian but I think decided that it was more shocking to be a Republican. In the 2000s, he has even called himself an "imperialist." I think it's a misguided attempt to shock people, rather than mean-spiritedness. Maybe taken too far, the two become indistinguishable.
I think you're right about Eat the Rich: it's just a bad idea to try to write a funny book that simplifies international economic realities. (It would be an equally bad idea to write a book taking an opposite political stance.) Like many ideologues, O'Rourke thinks the world is simpler than it is, and thus has no problem making over-broad generalizations.
And yes, Joe Queenan IS funnier. He used to be one of my favorites, but then his weird take on BORAT turned me off big-time.
I disagree with people who say that Borat was just mean-spirited, particularly as he usually just allows people to embarrass themselves. But the anti-American charge is weird. The Borat skits in Britain were pretty much the same as the American ones. Making fun of particular Americans is not the same as being anti-American.
Meanwhile, Queenan's "Red Lobster, White Trash, and the Blue Lagoon" is one of the most elitist and anti-democratic books I've ever read. (Funny, though.) SBC makes fun of people for being bigots, which I'm fine with. Queenan thinks he's better than the plebs because he has good taste. I stopped judging people based on what movies they like when I stopped being a teenager.