8. Adam Milligan
Location: Inside Lucifer's Cage in Hell, with Michael wearing his meat suit
First Appearance: Season 4, Episode 19 "Jump The Shark"
Played by: Jake Abel Showing up in the aptly titled Jump the Shark (shows often go south when they reveal a long-lost sibling) third Winchester brother Adam has had a really rough road of it. When the Winchesters first met him, he wasn't even Adam, but a ghoul that had taken their brother's form. Later, he's pulled out of his private Heaven where he's smooching on his Prom Night and lands back on Earth so he can play vessel for Michael in the throw-down with Lucifer. When Michael takes Adam's body anyway, and ultimately ends up falling into Lucifer's cage with Sam, he's seemingly trapped there and never escapes. This for me, has always been the most galling post-Kripke plot thread and casts real suspicion on the supposed "family first" tagline that Dean and Sam so fiercely hold to. Yes, back in season 6, Dean did ask Death if he could rescue both Adam and Sam's souls, when he was given the choice of only one he said Sam and has never ever looked back. Granted, they have had plenty to contend with, but not once have Sam and Dean talked seriously about mounting such a rescue mission for their brother, who by now--if Michael didn't get them both out by some other means--has suffered far, far more than Sam did. In Earth time three years (!) have passed since Adam was trapped in the Cage. Of course, the question is also raised of why Castiel didn't also pull out Adam's body when he went in looking for Sam's. I've often waited for the revelation that Adam and Michael were no longer in the cage when Castiel got there, but I'm pretty sure that's been debunked in references to Sam's soul being caught in Michael and Lucifer's feud. No matter, because Adam's thread still remains unresolved, and at this point the show owes the character something more than a five minute cameo to resolve the situation. Actor Jake Abel has matured since the close of season five, even though he did a fine job there as Michael. Bringing this Winchester back, but setting him apart from the other brothers would add a certain connection to the parent show that would help merge the two properties. Besides, it would be nice to have one Winchester out there who didn't have to worry about his sibling every time he so much as used the bathroom.