4. Crowley
Location: Usually Hell, Right now, in the custody of Sam and Dean, and crying like a little girl
First Appearance: Season 5, Episode 10 "Abandon All Hope..."
Played by: Mark Sheppard He's basically Supernatural's version of William "Spike" the Bloody, a villainous cameo that was so well received he kept coming back until he achieved prime Big Bad status, and now might be headed on a similar road of bewildered repentance, wherein one can only assume he'd possibly become a begrudging ally of the forces of good. Right now, it's almost impossible to imagine the King of Hell, who has done any number of reprehensible things in the name of evil, going soft to the good side, but outside of killing Crowley it's hard to know what to do with him. He's just about run his course as the big heavy, and Mark Sheppard's performance, although easily carrying the character thus far, seems to be getting a bit bored with the one-note villain schtick. Add Crowley to that list of characters that would be legitimately interesting as a good guy because his nature is not milquetoast or quaint; no matter what side he's on, he's going to run you down, belittle you and bitch and moan the whole way, usually in a very amusing manner. Sure, if Crowley gets cured, it's the end of Hell, so while that may not happen, what if he remains a conflicted demon with powers? I can't seem him staying with the Winchesters, but stepping in as a grumbling, snuffling mentor to monsters somewhere else might be legitimately interesting. I'm all about Crowley in any form, but I think it's time for a change and this could be a very good one. Sheppard definitely has what it takes for a regular weekly gig, and if you need evidence of him as a good guy, look no further than Matt Smith's second season of Dr. Who, where he played Canton Delaware in "The Day of the Moon" and "The Impossible Astronaut".