July 16, 2008--Depending on whom you ask, the July 21 cover of The New Yorker has become cause for outrage, confusion and partisan glee. Given the flare-ups surrounding race and representation that have rocked the 2008 presidential race, it's easy to treat the satirical cover—of a be-turbaned Barack and a be-afroed Michelle Obama—and other "racialist" images of the couple as a serious problem. But when it comes to cartooning, the presumptive Democratic nominee has gotten a bum rap since day one.

During Obama's meteoric rise from state senate to the threshold of the oval office, political cartoonists have had to grapple not just with a fresh face to draw, but a new race to signify. Photographs of Obama's angular, open visage—half white, half black—have graced countless magazine covers in the last year alone, appearing at times Marvel-esque, at others proletarian. His cartoon self, however, has been wildly incoherent.

Drawing a black man—either seriously or satirically—it appears, is damned difficult.

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Let's start back in December 2006, with a cartoon drawn in the months fraught with speculation just before Obama announced his candidacy.

In this image, the artist, Lisa Benson, gets the "black" nose right, and provides a fuller lip than many political cartoonists are accustomed to—but as a result, Obama and his elderly female companion might as well be Bill Cosby and Estelle Getty from The Golden Girls. Seriously. Riding behind Obama, Estelle demands: "Thrill me!"—and there is a hint that if not, her old-lady purse may come a-whacking. The good rocket "Obama 2008" is, slyly, shackled by the supermarket parking lot in which it resides, but the resemblance to Cosby is telling: like (a slimmer) Heathcliff Huxtable, Obama is meant to entertain—perhaps only for the span of a 25-cent amusement.

Here is another drawing from late 2006, in which Obama is depicted as the antidote to Hillary Clinton's nomination, then presumed to be inevitable:

Apparently, another political meme from back then—that Obama was "not black enough"—made it through to the cartooning zeitgeist. Granted, the black-and-white format makes it difficult to portray a biracial subject—but here, Obama's features are distinctively white; aside from the chin (and the sharp edging on his 'do) he could be a young Nixon—or, frankly a dark-haired Dick Gephardt. The artist hasn't even bothered to daub Obama's face with the cross-hatching used on the bricks at Dem HQ.

Another period cartoon demonstrates the unformed image of Obama posed in the early days of his candidacy.

In this ad, also from 2006, the skin color is more appropriate. The ears are about right, too (they feature prominently), but the eyes are dead, and the jaw is all wrong. Here, a bit of a smile would have done more to evoke Obama than the dutiful "browning" of his skin. More interesting is the spectatorial nature of the cartoon's commentary. The badly-drawn Barack is once more a performer—a promising one, but, like an athlete or show horse, reduced to a set of statistics that somehow relate to the presidency—for better or worse.

The representations of Obama get a little better as the race heats up. In January 2007, we mark the debut of "the teeth":

Obama's signature smile, however, is accompanied by an image that looks more like a hybrid between him and Howard Dean (also mentioned). Just imagine—Dean's square jaw and bulldog neck; Obama's cheekbones and wide smile; both of their noses—it's a monster! Really. This Frankenstein Obama still boasts a bit too much forehead, and not enough expression around the eyes to qualify as even a passable likeness. But the smile is out—and boy, are those white people excited!