Obama's "lipstick on a pig" blunder is a reminder that he needs to hire a jokewriter so he can poke some much-needed fun at himself. Over the last dozen days, the whole race has wandered off into old-fashioned American comedy (what could Frank Capra have done with a Sarah Palin character?), leaving the new-fangled Obama rattled.
Jeez, when somebody makes a joke about the the stupid job you had when you were in your 20s, you make a joke back. You don't get all hurt, peeved, and self-righteous like Obama did about Palin's little "community organizer" witticism. Maybe his "lipstick" line wasn't aimed at Palin, but he ought to have expected that everybody would take it that way by now.
Obama's Achilles heel has always been that his gimlet-eyed appraisal of human beings doesn't extend to himself -- he can't keep from feeling sorry for himself. It seems like a hundred years ago that I called Obama "a close student of other people’s weaknesses, a literary artist of considerable power in plumbing his deep reservoirs of self-pity and resentment, an unfunny Evelyn Waugh..." (Waugh could never stop feeling sorry for himself that he was born into a merely affluent, respectable family rather than a rich, aristocratic one. Obama's sad "story of race and inheritance" is more complicated, but still rather similar.)
That's why Dreams from My Father reads like the Brideshead Revisited of law school application essays.
The GOP brain trust (if such an oxymoronic body exists) will sooner or later figure that out and try to spend the rest of the campaign poking and prodding Obama's delicate self-image to see what happens.
In one of his half-brilliant, half-wrongheaded insights, Spengler suggests:
"Combine a child's response to serial abandonment with the perspective of an outsider, and Obama became an alien species against which American politics had no natural defenses. He is a Third World anthropologist profiling Americans, in but not of the American system."
Sometimes, Obama reminds me of the persona Christian Lander invented for the narrator of Stuff White People Like: the mild-mannered but cold-blooded interloping observer/exploiter of upper-middle class Americans' self-delusions and status anxieties. (Perhaps Lander had Obama in mind?) Those traits can take you a long way, but Obama may have to show a little more to go all the way.