House of Games was the first film David Mamet directed, featuring Joe Mantegna as a con artist. My favourite line in the film is when he says, “It's called a confidence game. Why? Because you give me your confidence? No. Because I give you mine.” Some of the best management advice I've ever heard.
Howard Rheingold's Wired magazine on the Amish and their debate over whether they would adopt cellphones, Look Who's Talking, is an instructive meditation on the cultural impact of cellphone technology that was years ahead of its time.
Ray Kurzweil is the leading prophet of the Singularity, the idea that within our lifetimes technology will accelerate to transform our world beyond what we can imagine. Ninety percent of the time I think he's full of shit. I hope I'm wrong.
James Howard Kunstler is more likely right that Peak Oil is going to make advanced industrial civilization impossible, knocking us back to mostly nineteenth-century level technologies, though this won't be an entirely bad thing since it will destroy the suburbs, the creation of which he calls “the greatest misallocation of resources in the history of the world.” His mini-website Eyesore of the Month chronicles the horrors of our built environment; I have a favourite entry, of course.
Sex at Dawn is a book about sex and human biology which is astonishing both because of what it says and because it dips into evolutionary psychology without turning into bullshit.
The Infamous Brad has an essay Not That the Actual Forbidden Knowledge is as Interesting as That There Is Forbidden Knowledge which explains Sudden Infant Death Syndrome. You may not want to know.
The Starship and the Canoe is a fascinating book about the physicist Freeman Dyson and his son George. There's an anecdote in there that I call the ninety second intelligence test. I won't tell you what it is, but if you meet me in person I'll perform it on you.
And I think that Digby is the most important political commentator in America.