I don't know if I think the OSR is going to diverge from 'mainstream' RPGs like the current edition of D&D and become a kind of 'alternative' aesthetic counterpoint like the weird and perverse underground comics once provided for the more wholesome mainstream comics from Marvel, Dell, Gold Key and DC. But I think that would be a viable alternative vision of what these publications can be for individual members of the OSR to pursue if they choose.I think we have already diverged. So far, with the exception of Zak/Raggi, that divergence isn't particularly deliberate or forward-looking. That doesn't make it bad, it's just that a lot of it has been driven by some other factors. These: (1) we generally started on lulu, even though we may generally be starting a move to RPGNow, and lulu's price on interior color pages is very high. To keep prices affordable, we've de facto gone with b/w interior art. (2) We generally have been looking to aesthetics defined by Trampier or Otus back in the day. By definition, we're a retro community, and that has been reflected in the art. (3) With small expected sales, investing in color art for internal pages would never recoup the cost.
In a sense, that harks back to an interesting effect. The art style and subject matter coming from Trampier and Otus is actually very close to underground comix. It's not on the weirder side of it, but it's not exactly mainstream. Which means that by being retro we have actually moved into an artistic forefront ... what's old is new again, and we are the new black. Again.
Will the OSR become a platform for a more avant-garde underground comix type of aesthetic beyond the extent where we're already there? That's an interesting question, but I really think it's worth noting that:
1) We already have a different underlying type of fiction that we're adapted to. Our talking heads are pretty sword-and-sorcery oriented rather than high-fantasy oriented. I don't know if we shouted down the high-fantasy guys with internet punditry, or if this represents a real trend in the OSR.
2) My guess is that even the high-fantasy guys in our community see head-shop hobbits in the mind's eye rather than the slim and trim ninja halflings. Take a look at some of the 1970 art having to do with Tolkien, and remember how people interpreted the hobbits' love of pipeweed and mushrooms. Tom Bombadil's hippie love. Go ask Alice about Tolkien when she's ten feet tall.
When you've got a different underlying story, you get a different underlying aesthetic. So we might not be at the "movement" type of point where Stefan sees the potential for us to go, I just want to point out that we're already more than half way to what he's describing.
I'd not be interested in seeing our art get into some of the realms explored by the underground comix, but in terms of the style, technique, and basic subject matter, we've already become almost avant gard, almost by accident.