Jensen's Wonky Eye
Lazy, wonky or just like staring into the sun? You can judge for yourself whether you think Jensen Ackles really has a wonky eye, but this is where its use in fandom originated, or at least spread into wider usage.
Win_non_con is a challenge which is held at the same time was the WinchesterCon, to provide some crack activities for those not attending the con. In the Second Win Non Con challenge in October 2007, one of the challenges was to find people’s "LJ Interests" that listed unusual Jensen or Jared body parts. The winning team rockpapersalt, whose entry is here, listed amongst their answer to this "Jensen’s wonky eye", as found on the journal of giventofly37. After the competition a few people added "Jensen’s Wonky Eye" to their own interest list.
For a while in fandom it was used as an ironic way of referring to Jensen’s perfect beauty, and also to allude to a subject of controversy (as in "Ask me about anything but Jensen's Wonky Eye") but now generally it is used to just refer to Jensen's Wonky Eye.