I have not had to do this in awhile.
We just had so many good entries in the previous contest and no clear vote winner I just couldn't pick which one should win. So I test entries on the image itself to see which words fit best. I was down to 3 by Alycat22, @SPNNeverSaid, and the one who actually won, Jennifer. Good job all.
Now let's see...
Poor S3 is still light on entries, so now let's pull an image from its finale! Wow, this was a dark show back then. Both for images and just subject matter. Not a lot of possible comedy clips... oh! How about Ruby (or Lilith) and Sam here? From episode 3x16 "No Rest for the Wicked."
The first 50 winning entries are here. Winning entries numbered 51-100 are here. The winners of 101-150 are here. And 151-200 are coming soon.