To be a great artist is inherently right wing. A great artist like Dylan or Picasso may have some superficial, naive, lefty things to say, but underneath, where it counts, there is a strong individual, taking responsibility for his place in the world and focusing on that.
Althouse is engaged in a bit of "South Park Republican" analysis here, ignoring mountains of disconfirming evidence in order to lay claim to an artist she likes as "right wing." Leaving aside the specious claim that there's anything inherently right-wing about being "a strong individual, taking responsibility for his place in the world," (which is the kind of thing you'd more expect from a fifteen year old who just read Atlas Shrugged for the first time), if Althouse thinks those things accurately describe "great artists," then she needs to get herself a library card.
I'm seriously not interested in arguments over artists' political tendencies, and I think that any political significance that attaches to art does so regardless of the particular views of the artist herself. The significance of Dylan's work, indeed of Dylan, is largely unrelated to who Dylan actually is as a person. But just to play the game for a moment, I think that a good artist is skilled at making and wearing masks, at representing different characters and points of view, and at highlighting ambiguity. Dylan is certainly a good example of this. If you want to consider whether these thing are left or right wing, have at it. I suggest that it has less to do with any particular character type that with how an artist serves his work.