Fifteen seasons is a lot of episodes for any show, and with that comes a lot of guest stars, and thankfully where Supernatural is concerned, we have a litany of memorable and in some cases improbable side characters. For the purposes of clarity, I’ll only be including side characters that have fifteen appearances or less, so don’t be expecting any Castiels or Crowleys in this list. Without further ado, we have the top five Supernatural side characters…
The first on the list of top five Supernatural side characters is the misfit with the mullet, Ash. He’s introduced when the brothers end up at a wayside bar frequented by hunters and having been to MIT, Ash provides invaluable information on the Winchester’s hunt Azazel, the Yellow-Eyed Demon, as well as later on in the show, how exactly to traverse Heaven. His appearances whilst short were always fun and in my opinion, he was wasted with his relatively early death, in not only what he could have provided help-wise, but also with his wit and sarcasm.
4. The Scooby Gang
Do you think when Supernatural was pitched to the studio executives, the creators or showrunners thought they’d ever have an entirely animated episode guest-starring the entire Scooby Gang? In one of the best episodes of season thirteen, the brothers are transported into an animated adventure where the Scooby Gang find themselves in the middle of a real ghost problem, one not easily solved by pulling a mask off some aggrieved fisherman or despondent family member.
Back in season eight when Dean is transported to Purgatory, we’re introduced to Ty Olsson’s Benny, a New Orleans originating, long-dead vampire, that decides to help Dean survive in the inhospitable and dangerous environment. Sticking to his word to Dean, he manages to stay clean of human blood, even going so far as to help kill another vampire, and in a show of true selflessness, agrees to go back to Purgatory for Dean, in an attempt to save Sam who’s trapped there.
Played by Sterling K. Brown, Gordon is introduced in the early seasons as a hunter that has his own means of killing the monsters. His methods leave a lot to be desired, and he ends up at odds with the two brothers, and ultimately his downfall is brought about once he finds out about Sam’s ‘demonic’ abilities, his death is one of the more inventive and gruesome improvisations by Sam or Dean throughout the show.
An obvious number one in the list of top five Supernatural side characters, what’s not to love about a wise-cracking, almost malevolent trickster in Loki, that then ends up being revealed as one of the four archangels of the Lord, Gabriel? Only having twelve appearances throughout the fifteen seasons, he transforms from a manipulative, reality-twisting villain, to a prominent piece of the puzzle that helps the brothers win more than one battle. I wouldn’t be particularly mad if they announced a spin-off of Gabriel and his adventures, such as the interest in the character.