Dean Winchester

Dean is shown to be understanding, kind, funny, mischievous, and, in contrast to his younger brother, a little immature. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him "raised like a warrior". He seemed to prefer hunting the supernatural over any normal "apple pie" life, though it was revealed that when he was sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn't leave Sam. This however did not last long, as later on while still sixteen, following a werewolf hunt he realized just how unique his life was.

Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, make sexual innuendos and indulge in pornography (especially for Busty Asian Beauties). Dean typically avoids emotional intimacy, Dean seemed to give up on ever having a family other than his brother.