Dave's Still Thinking It Over

Douglas MacKinnon ponders what David Letterman will do in January of 2009, when he doesn’t have fellow boomer George Bush to attack nightly:

In now a famous “You Tube” moment, Bill O’Reilly of the Fox News Channel, went on Letterman to be the recipient of the host’s rude and sophomoric antics. As the segment shifted into high gear, O’Reilly asked Letterman a pointed and direct question: “Do you want the United States to win in Iraq?”To the surprise of no one but his sycophants, Letterman could not or would not answer the question. When pressed by O’Reilly to answer, the best he could do was to play to his mostly left-leaning audience for cheap debating points and say, “It’s not easy for me because I’m thoughtful.”

How thoughtful do you need to be? it’s an A or B question: do you want the US to win, or Al Qaeda, the Baathists, and Iran? Letterman, who, 20 years ago, was once the master of postmodern irony, became its unintentional victim as he unwittingly echoed Jack Benny’s classic gag when he retorted to a fictional mugger shouting “Your money or life, pal!” on his old radio show: “I’m thinking it over!”

But then, as Bill Kristol writes in today’s New York Times, much to its ombudsman’s chagrin, “It’s apparently impermissible for leading Democrats to acknowledge — let alone celebrate — progress in Iraq.”

Update: Related thoughts from James Bowman:

Just look at the campaign on behalf of Darfur. “It’s not a political issue,” says superstar heart-throb George Clooney. “There is only right and wrong.”

Following the Letterman thesis, that’s not very thoughtful at all, George.