What would you call a group of experienced monster hunters going on exciting adventures, occasionally being brought back from the dead or going toe to toe with gods? If you said a D&D party, you'd be wrong! Instead, this almost perfectly describes the lives of the Winchester brothers as they face off against pretty much every supernatural creature in existence.
But what if the Winchesters and their rotating cast of allies and enemies were living in a Dungeons & Dragons world? The shows addresses many extremes of good and evil across its staggering 15 season run. What if we applies some D&D logic to those themes, and figure out what alignment best fits these Supernatural characters.
10 Charlie Bradbury (Chaotic Good)
This fan favorite character first appeared in season 7 working as an IT expert at Richard Roman Enterprises. She helped Sam and Dean defeat the Leviathans and was instrumental in translating the vital Book of the Damned before she met her end in season 10. She was a self-identified huge nerd, as well as being brave and incredibly smart. She's clearly good-aligned, risking her life to fight against the forces of evil. She's also chaotic because she has no particular reverence for law and order; she's a hacker with a whole slew of aliases to throw law enforcement off her trail.
9 Ruby (Lawful Evil)
Ruby was originally a regular human living through the time of the Black Plague. She sold her soul to become a witch and was eventually turned into a demon herself. She was a major influence in early seasons, being the primary negative influence on Sam as she manipulated him into becoming Lucifer's perfect vessel. Obviously supporting the rise of Satan makes her solidly evil-aligned. She also explains that she was the best and most loyal of Lucifer's followers, so deep undercover that even other demons hated her. She couldn't have played that kind of long con if she tended toward chaos.
8 Kevin Tran (Lawful Good)
Kevin has been through a lot. He was just a kid when he was called to his destiny as a prophet and got mixed up in the Winchester's never-ending crusade against the forces of evil. But when he saw the kind of danger the world was in, he stepped up to the plate and joined the forces of good.
He was committed to providing any assistance possible to the Winchesters, using his special ability to read the Word of God to help them. He grew a little bitter over time, feeling like none of his allies actually cared about watching his back, but because of his commitment to his cause, he stayed until the very end.
7 Gabriel (Chaotic Neutral)
Chaotic neutral characters are the bane of many DMs because of their tendency to do whatever they want whenever it pleases them, plot be damned! Gabriel, who spent his time on Earth masquerading as the Norse god Loki, embodies this perfectly. He's a trickster spirit just looking for a good time. He wants nothing to do with his family's "drama". He'd rather snare the Winchesters in a Groundhog Day-scenario or trap them inside a TV than risk his own skin—at least until the whole world is at stake, because hey, the world includes him too!
6 Lucifer (Neutral Evil)
The Big Bad, the fallen archangel, the King of Hell himself. Of course he's evil. How could he not be? His utter contempt for humanity saw him breaking from his holy family and being cast out of heaven. Since then he's been systematically corrupting human souls and twisting them into demons, using them to sow more even more misery among humanity. His desire for the destruction of humanity might make him seem chaotic at first, but he has to patient enough to ensure he'll strike when it does the most harm. We think he's neutral evil—just the plain ol' archetype of all the evil in the world.
5 Bobby Singer (Neutral Good)
Bobby spends most of his appearances in the show acting as father-figure to the Winchester brothers, filling the role better than even their own father was able to. He could be brusque and sometimes harsh, but always did what he felt was best for the boys, unlike John who always did what was best for his crusade.
In a perfect world, Bobby would be left alone to his scrapyard and his beer. But when his family and the world were in danger, he proved to be a very valuable ally. The Winchesters wouldn't have made it out of many scrapes without Bobby watching their back or giving them necessary information on their target.
4 Crowley (Lawful Evil)
Crowley's been able to call himself both King of the Crossroads and King of Hell, and what is a king without laws to uphold. Crowley's a demon and, despite occasionally serving as ally to the Winchesters, is still evil at his core. He's out for himself and doesn't care who he has to hurt to get what's his. But the way he does it is exceptionally lawful. He turns Hell into a never-ending line that souls have to wait in. He's always making deals. His past as a crossroads demon instilled in him the ability to follow through with the exact letter of his contracts and still get exactly what he wants.
3 Castiel (Chaotic Good)
Angel of the Lord and close ally to the Winchesters, Castiel is perhaps one of the strongest forces for good in the entire show. He experiences some doubt and occasionally believed himself a danger to his friends, but when it comes down to it, he just wants to save the world and the people he's come to care about.
Angels in general don't lend themselves toward chaos, but is, of course, fallen. Because he rebelled against his orders and continued to do what he thought was right, he was cast out of Heaven. And rebels are the best example of the chaotic good alignment.
2 Dean Winchester (Lawful Neutral)
Now we're down to the brothers, the heart and soul of the entire series. Dean Winchester followed closely in his father's footsteps and truly believed in John's mission of revenge against the monsters in the world. However, he cared even more for his family, namely his brother. While he doesn't have much respect for the letter of the law, being lawfully-aligned can also mean adherence to tradition, which Dean has in spades. If Sam didn't get it into his head to break from that tradition, Dean probably would have gone on following John's lead forever. Luckily, his loyalty to his brother was stronger.
1 Sam Winchester (Neutral Good)
Out of everyone in the show, Sam is probably the moral core, especially in earlier seasons. As time went on, they all became more jaded. But Sam always wants to ask questions before they shoot and was willing to spare a "monster" that didn't mean anyone any harm. The forces of darkness have to work long and hard to try and tip them over to their side, and even then they had to convince him it was the right thing to do. When it comes down to it, Sam took more after Bobby than he did his father: more brain than brawn, and more heart than instinct.