Brian,
Those remind me of Shel Silverstein illustrations.
In the very early days of the Jackson movies there were a lot of Tolkien sites that featured amateur artwork. Basically, whatever got sent in was posted by the site admins. Some of it was real kiddy-stuff, but some quite poignant considering the age of the contributors. I really enjoyed those sites but most of them seemed to have closed down as a few large and/or 'official' sites dominated the net.
Independent boards like the one you linked to might be the next best hope for really different interpretive art.
Speaking of which, it's not art, but what happened to the Annoted LotR that the TORC posters worked on and wilko put up on a website? I read it when it was first being loaded but then wilko stopped work on it for awhile (I think when he was without a computer) and I don't know if work on it has resumed.
Maybe if wilko sees this he'll post the link.
Jn
_________________
"All things considered, I'd rather be in Philadelphia."
Epigraph on the tombstone of W.C. Fields.