The moving post-race frontier

I just had an incredible conversation with my father, sweeping across many topics and tying them all together in the end. My quote of the day: "Thank you for sparing me your baldness anxiety and putting on a brave face until I too started going bald."
Anyway, we got to the inevitable topic of Don Imus and his statement about the Rutgers women's basketball team. I knew exactly what my father would say. "Back in the old days people weren't sensitive like they are now. People these days can't say anything without getting strung up."
Actually he said those things, but also that Imus is a notoriously shocking racist and he's been saying much worse "right to Joe Lieberman's face" for years, so why now?
I know where my dad is coming from with the 'people used to be much more relaxed about race' thing. My father grew up in mixed company in Astoria, Queens. New York City was always a melting pot, and the guys my dad grew up with were Italian, Irish, Jewish, Greek, Eastern European et cetera. They came up together and gave each other the business on all sorts of stereotypes and racial humor. My father considers this to be a tradition being lost in the sensitive PC world we live in. I would argue that my father and the people he grew up with in New York were on the cultural cutting edge, and in fact are still ahead of their time. They took a bunch of hoary old ethnicities and built the new post-ethnic 'urban white' ethnic group as it now exists, and of which I and almost everyone I grew up with are a part. Case in point: a vast majority of the people in my high school had Italian last names, and yet this didn't seem to register to anyone ever.
The unfortunate downside of being on the cutting edge, as my father was, is that you tend to lose sight of where most people actually are, mentality-wise. I made the case to my dad that he and the men of his generation believe on some level that a free and open exchange of racial humor on the level of equals is a great force for deflating the power of racism, and thus you hear so many old white guys trying to imitate the way they think black people talk. I further argue that the reason this so often falls flat is that the racial humor is the result, and not the cause, of ethnic equality. Those Micks, Jews, Wops, Bohunks, Polacks and Greeks wouldn't have been able to have such a rapport if the underlying understanding of ethnic equality hadn't been present. John Randolph Huntington from Park Avenue couldn't have showed up at the ball park and started throwing around 'Herschel Spiccoli the Italian Jew who only stole wholesale' jokes, because it would have rung false.
Going on that little bit of logic, I postulated that that as the level of ethnic equality is constantly being extended, the actual comfort level of the nation as a whole is gradually catching up with my dad. While my father couldn't reasonably share racial jokes with Asians or Indians of his own age, I probably could with mine, within reason, and they certainly can among themselves. I raised the example of Dr. Ken, my new favorite comedian.

Here you've got a Korean American saying that Vietnamese Americans are "kind of gay" and "when they speak English they're like gay retarded deaf mutes" and doing everything out of the black hip-hop guy playbook ("Doctor Ken is in the hizzy! Pimps up Hos down West Siiide!"), unironically, I might add, and pulling it off with style.