The show thrives on this so much that sometimes it comes back to bite them in the ass.
- Sam:
- Is he truly pure at heart (in spite of his missteps) or a whiny and smug Ungrateful Bastard?
- Was he jealous of Gordon taking his brother (who also was one of the reliable parental figures he had) away from him, or was he genuinely concerned about Dean's latching onto a replacement father figure? Or did he have a gut feeling that Gordon couldn't be trusted? Or perhaps a combination of two or all three of those things?
- When he was soulless in Season 6, despite claiming to not care about Dean or anyone else, he risked his own life to save Dean on several occasions when he could have just left his brother to die. Was he saving Dean because he was useful to him, or did he feel some kind of attachment? Or was his soul somehow able to have some small amount of influence on him despite being in the cage?
- Dean.
- There's no denying he has a bit of a martyr complex. Is it saintly or just unhealthy?
- Dean's Handsome Lech tendencies: funny and harmless, or compulsive and slightly sad? Is he really a charming playboy or is he just a "do-and-ditch" type with Commitment Issues? And if it's the latter, to what extent is the issue due to his life as a hunter? Add the fact that Dean is also a Blood Knight.
- Dean's attitude towards Sam: selflessly looking after his brother no matter what, or is he selfish, controlling, self-righteous, and even abusive? And because of that, depending on how you look at it, Sam could either often times be an Ungrateful Bastard or justifiably defiant when it comes to ignoring his brother's wishes.
- John Winchester: a once good man broken by loss and tried to do the best that he could, or a callous bastard who emotionally abused his children in his obsessive desire for revenge? In-Universe, the characters themselves seem to vacillate on which one they consider him to be. It's also possible that he started out with the best intentions but gradually lost himself to hatred in his quest for revenge.
- Ruby: did she truly care about Sam or was she just using him to raise Lucifer? One could use evidence drawn from the previous episodes to argue that her apparent concern and happiness for Sam were always all part of an act designed to keep manipulating him for a scheme she didn't survive to follow up on, or as simple mind-games used to toy with Sam. On the other hand, one could also use evidence drawn from those same episodes to argue that that Ruby did love Sam... as best a demon can love a hunter, at least, with all the intentional/unintentional cruelty and delusion that entails. For their money, Eric Kripke and Genevieve Padalecki both state that Ruby did love Sam in her own way, but whereas Eric felt that Ruby thought that she was doing what she thought was best for Sam and was well-meaning at heart, Gen theorized that Ruby's "love" for Sam came from his power and possibly (though Gen didn't mention this part, since it was before The Reveal) her knowledge of his destiny. Of course, it's possible that Ruby started out as just seeing Sam as a means to an end, but her feelings for him became real somewhere along the way.
- Castiel: Is he a naive, socially awkward but well-meaning angel who selflessly devotes himself to his friends and gets abused and taken advantage of? Or is he an amoral, calculating, borderline sociopath on a power trip who gets off on controlling and manipulating everyone around him? At the end of Season 6, did he betray the Winchesters, or did they betray him? Or both? Was he really trying to save the world, or was he just Drunk With Power by that point? There was some, ahem, heated discussion about this following the Season 6 finale. Later seasons pretty much confirm the "well-meaning angel who selflessly devotes himself to his friends and get taken advantage of" interpretation, as he deeply regrets his actions, becomes a Death Seeker out of his guilt for all of the damage he has done and develops a deep-seated desire for redemption, which the villains repeatedly take advantage of. His guilt and desire for redemption also leads him on a quest to make things right with his vessel's family, especially Claire Novak.
- Lucifer: Originally in Season 5, he was presented as a Not-So-Well-Intentioned Extremist with Affably Evil and Faux Affably Evil shades — though at times he expressed a really black sense of humor, and had no qualms about killing his own demon servants to further his own goals or killing pagan gods just because they made him sick, he also extended mercy and sympathy to his foes such as Dean multiple times. From Season 11 onwards, he's presented as a gleeful Card-Carrying Villain, which begs a question — was he always like this and just knew how to hide it, or did he only become this following his Villainous Breakdown in the S5 finale? The last few episodes of Season 13 pretty much confirm that it is the latter.
- Michael: Is he truly a Well-Intentioned Extremist who has resigned himself to the belief You Can't Fight Fate and believes he is doing God's will by ushering in Paradise? Or does his Extremism conceal the Freudian Excuse that he's really just a cosmic Manchild who wants his daddy back, and thinks continuing to do as his father told him to is the way to go (just like how Lucifer is ultimately a cosmic Manchild crying for his father's attention by wrecking his toys)? Or is he a slice of both inter-layered with each-other?
- Is Raphael a Well-Intentioned Extremist of a more pessimistic brand than Michael, who's truly just sick of the corruption and suffering occurring on Earth and being forced to run Heaven in God's absence, and he just wants the Apocalypse to bring Paradise and give him peace and an end to all that? Or is he actually a power-hungry Not-So-Well-Intentioned Extremist, who believes he and his brothers can do whatever they want with the universe in their Father's absence and is willing to stoop low just so he can be the new God? His portrayal in Season 6 seems to lean towards the latter.
- Was Anna following Heaven's orders or not in "The Song Remains the Same"? There's just as much evidence to support one as the other. In-Universe, she even argues about which one it is with Cass. Moreover, was she the villain of the episode trying to murder the Winchesters even after they helped save her, a very dark, very desperate Anti-Hero / Anti-Villain using evil methods to prevent a worse outcome, a Hero Atagonist trying to undo the Apocalypse by making it so the heroes never existed, or a Brainwashed and Crazy woobie and scapegoat who is made to suffer for actions that she has no control over and would have been appalled by in her normal state? Or was she even there doing those things at all, given how archangels have mental projection powers and Michael could have made the Winchesters and Castiel hallucinate the whole event rather than even needing to use the real Anna for Engineered Heroics.
- The angels in general: are they a bunch of petty, self-righteous Knights Templar or are they deeply damaged by their father's Parental Abandonment and not handling it well?
- The demons in general: are they creatures of pure evil who Rape, Pillage, and Burn purely For the Evulz, are they in pain from centuries if not millennia of torture and lashing out like wounded animals, or do they see humans as a bunch of hypocrites who are just as bad as them but don't admit it? The demons in the first episode of Season 3 and the demon possessing the bartender in a later episode of that season point out various atrocities committed by humans as a "Not So Different" Remark. Of course, given that demons lie all the time and most of the things they say are carefully worded in such a way that it'll mess with your head, it's hard to tell.
- In "Time After Time", was Chronos an unrepentant monster who killed only to fuel his own powers, or was he genuinely tired of millennia of involuntary "Quantum-Leaping" through time and honestly believed his victims were necessary sacrifices so he could remain tethered to 1944 and be with the woman he loved?
- In "Sacrifice", was Jane really the only Nephilim in existence or was Metatron simply lying to Castiel in order to get him to kill "an abomination" as he saw it? Considering that he repeatedly lies to Castiel about what they are doing, this throws the rest of his claims into doubt as well?
- Is God a benevolent father figure who truly cares about humans and angels, but values free will to such an extent that He refuses to directly intervene and be a literal Deus ex Machina? A well-meaning, but imperfect creator who really cared, but couldn't prevent things from falling apart? Or a hypocritical jerk whose blatant favoritism of one child and then another and eventual leaving make him a deadbeat father at best if not a cruel, capricious jerk who set everything up for his own amusement? The Season 14 finale confirms that he is the latter.
- Did Ava Wilson really get Drunk on the Dark Side, or (like Jake originally intended to) did she secretly plan to kill Azazael (who had murdered her fiancee, after all, which could have left her wanting revenge) to stop him once she was the last special child left, and see killing the others as being Necessarily Evil to ruin his plans? Or, like Jake, did it start out that way and lead to her genuinely being corrupted?
- For that matter, some fans wonder if, rather than Ava controlling the atypical breed of demons from that episode, they were possessing her for at least part of the episode so that being betrayed and attacked like that by one of their own would make the last Special Children more willing to kill each other and listen to the corrupting words of Lucifer.
- Did Cain really intend to kill Dean and the rest of his descendants like he claimed, or did he cross the Despair Event Horizon and want Dean to kill him because he knew he couldn't fight the Mark's influence anymore? The fact that he keeps provoking Dean throughout the fight and chooses to Face Death with Dignity after being defeated suggests the latter. Also keep in mind that with his power, Cain probably could have killed Dean easily, especially after taking the First Blade from him, but he insists on toying with him, taunting him and monologuing about what the Mark will do to him. Although Cain does eventually try to kill Dean with the First Blade and almost succeeds, that could be the Mark briefly taking over.
