Kill, Bill
In this Washington Monthly article, presidential jokesmith Mark Katz describes working with funnyman Bill Clinton. (Thanks to Greg Connors for the link.)

An excerpt:

My first assignment for the newly inaugurated President Clinton was to draft a page of jokes for his upcoming appearance at the White House Correspondents Dinner in 1993. Most of my suggested jokes were on the topic of his bumpy first hundred days in office. He leafed through my draft, his face unlit with enthusiasm. "Enough jokes on me," he said. "We need to do more jokes on all of them," meaning the media. "I thought this was a press dinner where I get to make fun of the press."

I realized then that we had arrived at a fundamental dividing line. I took for granted that the endgame of these ritual humor dinners was to ingratiate oneself to the audience--in this case, the press--and that the speaker should be his own primary target. From what I could tell, this did not come naturally to Bill Clinton. I had the feeling that he couldn't understand why we had handed him pages of self-deprecating jokes to tell to the people who deprecate him for a living. To him, it must have seemed like appeasing Torquemada by placing yourself on the rack until you confess.

This was also the symptom of the political culture shock of going from Little Rock to Washington. Clinton was raised in a political culture where gentle, self-effacing humor was all but unheard of, and political humor dinners featured a much meaner brand of funny. In Arkansas, I was told by people who'd know, humor is a stick that you beat other people up with. Clinton kept in his head a running list of the personal hypocrisies, professional double standards, specific unfair shots, and falsehoods uttered against him. He wanted to recite them all, and if they were expressed in the form of a joke, well, that was fine, too. But left to his own devices, the defining tone of his speech to the Washington press corps would be, "Katy, bar the door!"

A year later, when I helped prepare speeches for Clinton's upcoming appearances at the Radio and Television Correspondents Dinner and the White House Correspondents Dinner, the Whitewater scandal had dominated the newspapers for two weeks. Within the White House, I had by then become something of a humor evangelist, espousing to anyone who would listen a variant of the Twelve Step philosophy: things are only as bad as the stuff you can't joke about. I was eager to play high-stakes humor, and all of my instincts told me that humor's biggest payoff can come at the hour of maximum danger. Maybe on the long list of reasons why Whitewater was not Watergate was that this guy, the president, could stand up in front of three thousand rabid reporters and show the courage to laugh at the very idea.

The night before the speech, we sent a draft to the president; the night after that, a tuxedo-clad Bill Clinton took the podium to address the same Washington journalists who had recently made "Whitewater" a household word and opened with a geographic version of a time-honored line: "I am delighted to be here tonight. And if you believe that, I have some land in northwest Arkansas I'd like to sell you."