I usually don't go much farther than 2.5 in the Sam...I mean, Dean episodes when I re-watch Gilmore Girls. Initially, I enjoyed his character. Dean was bright, read books, and seemed to like Rory because she was smart. Midway through season one, those characteristics seemed to disappear in favor of a more bland boyfriend cliche (and Jess inherited his book smart qualities). Don't even get me started on what happened from season 2 onward.

Sorry for the ramble. I agree with you about the weirdness of seeing Sam Winchester in Stars Hollow. ;)