When: April 2008
Lou Dobbs
Watch it here: 
Dobbs almost calls Condi a "cotton-picker"

If Lou Dobbs isn't a proud reactionary, he's at least the most racially-unaware commentator of all time. In an apparent Freudian slip, the former CNN host countered Condoleeza Rice's claim that racism still existed in America by, well, illustrating her point exactly.

"Not a single one of these cotton...[stammering]...these just ridiculous politicians should be the moderator on the issue of race," he said, unaware he was part of the problem.