I don't really feel like thinking hard enough to make my point right now (because it's a very fine distinction, and I'm on my fourth beer), but I find myself saying similar things (proclaiming something to be "brilliant," when it's not even clear the person doing it was coherent at the time). Basically, knowing that your career comeback kind of depends on proving you "still got it" at this one important event--that's going to be watched by millions--yet still getting trashed and ignoring pretty much everyone else's advice before going on... I don't know. I've been on this kick lately where I obsess about things being "authentic," and shun anything that smacks even a little bit of being contrived. In the sense that, whether she knew she was doing it or not, this was the most uncomfortably authentic moment at the MTV award show, it *was* kind of brilliant. I'm not saying Britney is brilliant, just the moment itself.
On another note, go back and listen to "Panty Lies." Though it was released in 1995, Kim couldn't have written a more oddly personal song about Britney if she tried.
Either I don't understand the point of "repping," or I do and it really is pointless. Fortunately I'm colorblind, so it wouldn't make sense to concern myself with being concerned about it in the first place.