The last eight years haven't been kind to many, but political cartoonists did have George W. Bush's puffy face to expand, his ears to tug, and his policies to ridicule. The prospect of less easily mocked president is a challenge for cartoonists like Michael Ramirez, who is better than most at finding a way to satirize Obama and his policies without crossing lines real or imaginary. Fortunately, they'll have a long history to learn from.Master cartoonist Thomas Nast proved political cartoons could be used to subvert racism, as in this classic satire of whites congratulating themselves for the emancipation of slaves from an 1863 issue of Harper's Weekly:

Nast's cartoons not only crucially challenged the way people saw political issues — coming as they were in a time with significantly less media — but they consistently fought against racist caricatures of black people. The issue of Obama's blackness will presumably become less of an issue after the election, and of course, Obama isn't close to the first major African-American political figure, a proud history that stretches from Frederick Douglass to Anita Hill and Clarence Thomas. Bush cabinet members Condoleezza Rice and Colin Powell both offered their challenges, but they weren't as exposed as Obama will be when cartoonists will have to meet their deadline every day with no McCain in sight. We can only hope the treatment of Michelle Obama doesn't resemble how some cartoonists drew Condi:

Yikes. And a recent cartoon depicting Colin Powell as Benedict Arnold wasn't much better. Widely syndicated cartoonist Mike Luckovich describes his experience drawing BO in an interview with the WaPo:

And what about drawing their bodies? How do you see them? McCain is short and sort of barrel-shaped. ... Obama is lanky and the thing is, he's loose. He flows and he's got a nice cut to his frame. It's good because he's very slender and you can capture that. You wouldn't make him too rigid. So what characteristics make up the political cartoonist's dream? You want someone who's a bumbling idiot to be a president. And Obama's not bumbling.

This inescapable fact has led to overreaching. The first line crossed in the cartooning of Obama was of course the tragic Barry Blitt New Yorker cover of the senator giving his wife a fist jab dressed in terrorist gear, but now cartoonist Glenn McCoy has already caught flack this past week for his depiction of the candidate's prospective cabinet:

The question of finding the funny in the Democratic candidate goes beyond cartooning, of course. Comedians have gotten considerable mileage out of a Republican administration, and if we're looking at four years of 'The Barack Obama Variety Half-Hour', political laughs could be hard to come by.