Obama’s derisive tone surprises and dismays some of the people who’ve written jokes for presidents past.

“With these dinners you want the audience to like you more when you sit down than when you stood up,” says Landon Parvin, an author and speechwriter for politicians in both parties, and a gag writer for three Republican presidents (Reagan and Bushes I and II). “Something in [Obama’s] humor didn’t do that,” he said Sunday…

Former Clinton speechwriter Mark Katz calls Obama’s humor “a work in progress.” Katz recalls that before Clinton made his first White House Correspondents dinner speech, he asked his speechwriters why there weren’t more jokes about his political enemies. Clinton’s speech drew criticism after he inserted his own somewhat hostile jokes.

“He took aim at people he should not have aimed at,” says Katz. “He learned his lesson and took greater aim at himself. He learned that the right joke about yourself can be as Machiavellian as anything Machiavelli dreamed up.”