I’m to understand that this is a left-leaning publication showing it’s support for Mr Obama. I’ll just have to take your words for it, since that makes no sense to me. (Particularly having now seen some of the covers which were supposed to mock Mr Bush. Or support him by satirising his opponents, or whatever.)
I’m reminded of those threads where angry Americans lambasted an Australian advertisement for its purported racism. Except in this case I’m not angry. Context and culture are everything. 
But suppose for a second that Daniel Tosh decided to go for the white supremist audience. Suppose he decided to make a career out of telling racist jokes in a completely non-ironic way to an audience of genuine racists.
He’d do the exact same act he’s doing now.
Now compare him to Stephen Colbert. Suppose he decided to sell out and join Fox News as a real conservative pundit. His act wouldn’t make it if he was trying to do it for real.
I don’t think he would. His racist jokes aren’t funny in and of themselves - what’s funny is how unabashedly offensive they are, the fact that you’re thinking “he’s not going to go there, is he ? Oh my god he went even further”. Sarah Silverman has the same schtick of crossing the line twice.
But take the offensiveness and the exaggerated, impertinent arrogance away and the jokes fall completely flat. Ann Coulter isn’t exactly funny, is she ?
To give you (or anyone not familiar with him) an example, one of his routines starts by musing on whether black people would taste like fried chicken to a cannibal. Then he goes on to pile more racist stereotypes, does the same for Mexicans and Chinese people, whipping up the crowd as he goes. He culminates with a deadpan “White people taste like… sorry, you don’t eat white people. Those are the rules.”
Cue embarrassed silence from the (mostly white) crowd who was laughing a minute before. And then a beat later* that *becomes The Funny. That whole routine would bomb if the audience responded to the white people comment with “FUCK YEAH !”
That kind of comedy goes back to Don Rickels and All in the Family. It’s nothing new, and I have no idea whether it is good because it exposes racists for who they are, or if it’s bad because it perpetuates racial stereotypes.
Oh my goodness. Maybe the end of the world IS coming, because for the very first time since I’ve been posting here I actually agree with athelas. (I think I’ve agreed with Malthus hither and thither, so that’s no big deal. :))
I don’t know if I should be afraid or happy!
Except that the OP’s friend, and the writers AJ Plaid and Carmen Van Kerckhove who inspired him, are not actually white.
Google “Deconstructionism”. That’s all it is about. There is no “there” there, in it. But for some people, it’s how they prove they are “intellectual”, instead of being stupid shits who can’t come up with anything of value to their fellow man, so justifying their existence.
ETA:
LOL!
You might want to try googling that yourself, and perhaps actually reading the cites that come back.
Please run for office, I’ll vote for you.
As to the specific New Yorker cover, it was entirely a spoof of the conservative nontroversy over the “terrorist fist bump”, Michelle is a racist, Obama pals around with terrorists (which is probably how he found OBL come t think of it). It’s about as subtle as an Onion headline, and was hysterially funny to me.