I've read quite a bit from him, and I really, really love his writing style. He can make everything interesting, and to this day I still have the 23 Questions I Ask Everyone I Meet In Order to Decide if I Can Really Love Them on my facebook page, and had people answer it all the time. That part of him is really fun.
And really, that's what he does well, he asks some though provoking questions and makes interesting navel-gazing connections and seems to really be in touch with some parts of human nature that connect us all to things in a fun, hypothetical way.
My gripe, though, comes from what seems to happen when he doesn't like something or forgets that's he's funny and whimsical, where he suddenly starts writing like he's a really profound, philosophical writer. He becomes extremely condescending and holier-than-thou. For example, look up any of his opinions on punk music. He doesn't just say he doesn't like this thing, it becomes the worst thing to ever happen since Hitler, and if you like it, you a half-donkey shit baby who has no part in our society and how can you be so fucking stupid to have a differing opinion to I, arbiter of culture who knows all. His writing stops coming off as navel-gazing self-aware ridiculousness and starts coming off as someone trying to pass this off as academic.
But I still love reading his work. He's a hack, but a fun hack. It's just when I get to those points, it makes me need to take a break from him a while because it sours everything around it.
He also has a bad habit of not really making his point very well, and, really, it's not too important most of the time. This article, for example, he circles around a few times and his real point here he ends up making is the cultural significance of Seinfeld, because it's popular satire, so nothing really groundbreaking there. But he frames the article around his point that it's villainous, but doesn't really stick with that, or why it's important, or why it's villainous compared to other shows with bad people as main characters. It just kinda falls away into his writing.
I am interested, however, in how his fiction work is. I can see it really going either way.