i've been working on a piece on american cynicism (twain, bierce, and mencken: my peirce, james, and dewey), for what may end up being a volume of essays for suny.
one angle: so there's a basic narrative of american thought: you have the transcendentalists, incredibly optimistic representatives of an america with an open frontier. emerson and even thoreau kept expecting a transformed and redeemed humanity, more or less made possible by america. well, the second half of the 19th century would make any quasi-rational person think twice about that. so the supposedly characteristic american optimism is tempered in the pragmatists from a secular milennialism to meliorism; things might not be just about to be entirely ecstatically transformed, but things will get better and better if we work for it. this is the narrative you'll read in many histories of american thought; it's even more or less the one i've taught in classes on american philosophy. but one thing you have to realize: every narrative, especially one that neat and synoptic, is simplistic, distorting, and largely false.
what if mencken was sitting in intellectual history where his contemporary dewey is right now? then the whole thing looks entirely different i believe. maybe that sounds ridiculous. but first off, mencken was an extraordinary intellectual. check out the american language, an amazing scholarly achievement. he wrote 'treatises' on philosophy of religion (his treatise on the gods makes all the hitchens and dawkins stuff redundant, and it is so much better) and on ethics (taking a naturalistic darwinian view). he was the first american translator of nietzsche. he was certainly much more widely known and read than dewey in his own lifetime. mencken dropped out of poly high school in baltimore to work on newspapers, but he was, believe it or not, far more erudite than dewey: you can't believe at any given moment what the man knows, from the whole history of philosophy, religion, and literature to what music they're playing in the speakeasy down the street. also (obviously) he writes infinitely better than dewey, and unlike dewey he's hilarious. well there are some problems too, of course.
i want to say that american cynicism - like the ancient variety - is a profoundly affirmative philosophy. it looks squarely at all the human realities that emerson and dewey apparently didn't see at all: all the corruption, self-seeking, dishonesty, mediocrity, especially among our eminent legislators. and it laughs and laughs. no one was ever more delighted by america than mencken. he loved our clowns and con men, our "Knights of Pythias, Presbyterians, standard model Ph.D.'s, readers of the Saturday Evening Post, admirers of Richard Harding Davis and O. Henry, members of the Y.M.C.A. or the Drama League, weepers at chautauquas, wearers of badges, 100 per cent patriots, children of God" - if nothing else because they made for great insults and jokes. none of these folks, apparently, were known to john dewey. america gave him a truly hearty laugh. but he didn't write fictional redemptions; he lived in something resembling the real world, namely baltimore.
that too is central to 'america': keeping your feet on the ground, looking squarely at the dark side, rolling your eyes at the glossy propaganda that they're feeding you. seriously, stop talking to professors - who are incapable of independent or rational thought - and start talking to mechanics. well that can take you into a place of darkness. but it took mencken to a place of joy. vicious joy, but joy.
now narrating it all through the prags is useful for a 'progressive' orientation, and it does make history culminate in democratic socialism. and surely mencken's reputation has faded primarily for political reasons. but there are many ways this history could be narrated, and hence many places we might be headed. also mencken was just not that politically problematic except for his germanophilia.