I don't have too much to offer on this apparently new phenomenon, but from what I've been able to observe by watching The Cool Kids "Black Mags", Kidz In The Hall's, "Drivin' Down the Block", and Kid Sister's "Pro Nails" I can definitely say that whether or not this rapidly developing style is deserving of the title "hipster rap", it is not simply a continuation of "backpacker hip-hop" which has post-90s represented a conservative force even if it has seen a bit of apparent return with Kanye and Lupe. The latter two artists can be credited to some degree for the legitimization of "backpacker hip-hop" today (and Lupe with skateboarding), but their music in and of itself, whether you think it dope or not, is nothing too sharp of a break stylistically from traditional modern hip-hop.
But taking the inroads that the Kanye and Lupe genre and perhaps generation has made and carrying it to its conclusion by an even younger age group has prompted some (apparently, the bloggers...gasp!) to cast the result as "hipster rap". Check out Jay Smooth this week at illdoctrine.com and see what he has to offer on this subject.
Yeah, the older hip-hop generation isn't sure what to make out of it, indeed. But, you know what, they didn't and don't understand bling and Southern hip-hop either so why would we be surprised that so-called hipster rap evades them?
On the flip side you got those who are coming to its defense, but on conservative terms because it has all the obvious, trivial qualifiers of "real" hip-hop. Blogger Lynne d Johnson replied to Jay Smooth's vlog by saying,
...I'm not offended by it at all. I don't even see it as a movement. I see it as Detroit, Chicago, B-more, Philly, and other places some of this is springing from, as trying to have its own distinct sounds and style. Creative. Inventive. (And please don't say it's a trend, because it's not.) The amount of people that go to these shows and listen to this music compared to the amounts who listen to the autotune sounds of Kannye [sic] West and Lil Wayne is no comparison. Kanye and Wayne [yes, she is about to dismiss Weezy] are trendy.
(So now the "realness" of hip-hop is measured by having the smallest amount of supporters. I should drop an album. I digress.)
Is this a real apparent return by which hip-hop as a living content takes a new form that appears to "go back" or is it just a bunch of smart-ass youth who think it "ironic", as Jay says, to mock 80s hip-hop as young, bourgie white folks like to clown "white trash" people (folks who have mullets) with their sarcastic statement T-Shirts they picked up from Target?
For my two cents, while Jay could be correct that the term hipster has outlived its usefulness and should be disregarded (as has capitalism which I place a little higher on the priority list), I don't think it applies to black hip-hop teens, but still works quite well for white (or black) coffeehouse-hanging, Nietzsche-reading chess players who cynically proclaim the end of history.
Maybe the youth just can't explain it. Just as all generations have historically been unable in the beginning to articulate the significance of their new activity (either politically or culturally), our generation is no exception. If you watched the YouTube clip of Mikey Fresh of Kidz In The Hall on how he feels about the term, his opinion is that it is merely an extension of backpacker hip-hop. I don't agree, but it's always interesting to hear it from the source.
For what it's worth, I think the music is dope. I'm 28. I've been listening to hip-hop at least 20 years, have claimed it as my own for at least 15, and at no point will I be so stuck in my own categories of what "authentic" hip-hop is that I won't be able to appreciate what the next generation is able to innovate. But this shouldn't surprise y'all.
I ain't no hip-hop conservative.