5. Benny Lafitte
Location: Purgatory
First Appearance: Season 8, Episode 1 "We Need To Talk About Kevin"
Played by: Ty Olsson Benny isn't the first benign vampire that Olsson has played on Supernatural--he was also Eli in the second season ep "Bloodlust"--but he's arguably the most endearing and durabl as a character. First appearing at the start of season 8, Benny was Dean's battle comrade in Purgatory, where the two went on a rescue mission to find Castiel and then located a portal out of there. At first, Benny's Cajun-fried brio suggested a True Blood-lite kind of character, but after a couple of episodes dedicated to Benny and his tragic back story we quickly realized that the vamp was on the level, and truly the kind-hearted, earnest type that he seemed. He was a welcome presence on the show, and it was irritating each time Sam whined about him palling around with Dean. Of course not even Sam could argue, when Benny agreed to let Dean kill him again, so he could re-enter Purgatory and pull Sam and Bobby's soul out of there. What Dean didn't know at the time is that Benny never planned on coming back, willing to test his mettle in Purgatory instead of struggling with the thirst and the persecution of the real world. There's a big point made of the fact that Dean did not burn Benny's body in case they ever find a way to bring him back--just make sure he gets in line after Adam, guys--and if Benny comes back, it's not likely that he'd be going on regular hunting missions with the Winchesters because he disrupts that brotherly dynamic. Sending him to Chicago to be a part of a monster community that interacts with hunters seems so perfect, one wouldn't be surprised to learn that the writers have had that in mind for a while.