While good satire is very often offensive, offensiveness is only rarely good satire.
In defense of the now-infamous The New Yorker cover, David Remnick claims that the artwork "hold[s] up a mirror to the prejudice and dark imaginings about Barack Obama’s — both Obamas’ — past, and their politics."
But where's the "mirror"?
The illustration misfires so badly because it is far more literal than satirical and its target is unclear. As the ever-ridiculous Jonah Goldberg admits (via Atrios), "it's almost exactly the sort of cover you could expect to find on the front of National Review." Even G. Gordon Liddy boasts that "The New Yorker finally got it right." Surely, this kind of recommendation is the stuff of Remnick's nightmares (or should be): accolades from a writer for a magazine with a noted history of racism and an ex-felon with a hatred of democracy.
Likewise, Byron York, another wannabe parodist at the National Review, gloats that "privately, some McCain types admit they find the cover funny. And how bad can it be for your campaign when a national magazine, in an effort to take a shot at Fox News and talk radio, portrays your opponent like this?"
And there you have the problem: we see the reflections in the mirror (Obama and his wife), but the viewers distorting that reflection (conservatives, Fox News, talk-show gasbags, etc.) are nowhere to be found. Not only does the caricature miss its targets, it doesn't even suggest they're there.
As Kevin Drum points out, there was a way to do this well--but Remnick and illustrator Barry Blitt must have been too busy preening in front of the mirror.