Stephen Colbert (2006)
According to WHCA President Steven Thomma, the job of the dinner's comedian is to treat Democrats, Republicans, and the news media alike to "a little good-natured ribbing." In 2006, Stephen Colbert shattered ribcages and fractured funny bones. Remaining in character as a parody of a right-wing pundit, Colbert called an incompetent, criminal administration just that, through only the thinnest patina of irony.
For example, in summarizing the conservative worldview he and Bush shared, Colbert hit especially hard: "I believe the government that governs best is the government that governs least," he said. "And by these standards, we have set up a fabulous government in Iraq."
And at the end of his speech, Colbert made time to thank the gathered press: "Over the last five years, you people were so good—over tax cuts, WMD intelligence, the effect of global warming. We Americans didn't want to know, and you had the courtesy not to try to find out."
They say great comedy disturbs the comfortable and comforts the disturbed, which might explain The New York Times decision to not to comment on Colbert's performance, and the WHCA's booking apolitical impressionist Rich Little for the following year.