There is a giant and fundamental difference between the two covers. Political cartoons work because they are based on a truth and taken to an extreme. The McCain cover takes the truth of McCain's age and his wife's drug abuse and puts them together in an exaggerated way. That's funny political humor.
The Obama cover is not based on truth, it is based on falsehoods and there is nothing in the cartoon to indicate that it's humor is bases on the falsehoods instead of the truth. Therefore most of the people who see it will take it as a political cartoon that exaggerates the truth rather than totally fabricates the truth. Most of the right-wing knuckleheads in both the Democratic and Republican parties will see this cartoon as the exaggerated corroboration of the "truth" that Obama is indeed a Muslim and that his wife is a militant "Black power" African American.
So when Cenk wonders why Michelle Obama is not liked by whites, this cartoon is a large part of the answer.