20. Benny Lafitte
Actor: Ty Olsson
"“I know it’s hard to believe, but I haven’t always been this cute and cuddly.” -Benny Lafitte"
Dean Winchester can easily count how many people he has faith in. The list of those he can trust with his life is even shorter. Considering he lives in a world where people can change for the worse or be monsters (literally), this isn’t surprising. What is shocking is his friendship with Benny Lafitte breaks both boundaries.
Benny’s bond with Dean isn’t the only thing that puts him on this list. It’s his tragic story as well. Benny ends up back in Purgatory because he can’t adapt to life on Earth. It was sad because Dean loved Benny like a brother. The only other people he cared for like that were Sam and Castiel.
19. Mary Winchester
Actresses: Samantha Smith, Meg Donnelly
"“We’re family. It’s our job.” -Mary Winchester"
Mary was fantastic in Supernatural, but her younger self was better in the Winchesters. Actress Meg Donnelly showed why Mary was a legend in the hunter community. There wasn’t a monster she couldn’t slay. Seeing her in her prime was something to admire. Sadly, the show wasn’t renewed. Meg Donnelly showed potential and should get another chance to play Mary.
18. Billie
Actress: Lisa Berry
"“Hey, Dean. See you again soon.” -Billie"
Billie does not play around. She knows her job and takes it seriously. Unlike Death, she couldn’t be influenced. Not even the Winchesters could make her budge. Even if the world was ending, she wouldn’t budge. You have to appreciate her professionalism.