The award for the coolest character in the Supernatural series has to go to Dean Winchester. He’s the brother who’s been handed the coolest lines, the funniest quotes, and most importantly, the honor of getting to kill most of the main antagonists.
As far as kill counts are considered, Dean far outpaces every other character we’ve seen on the show, and these kills have come in a lot of creative ways. In this list, we’ve included the best “ganks” by Dean Winchester in terms of impact the deaths brought us, as well as the appeal in watching the kills play out.
Gog and Magog
We’d hardly ever seen Dean display true fighting skill before his confrontation with Gog and Magog, and witnessing it confirmed that the elder Winchester sibling did have some serious moves.
Gog and Magog were supposed to have god-level of powers, and Castiel was even easily beaten by them. Dean on the other hand, went straight for the weak spots, and hit the main pressure points of his much larger opponent, bringing him down and eventually killing him. He would then follow up by saving Castiel and taking out the second bad guy as well. All this while being a normal human - a pretty badass one at that.
Purgatory Kills
Dean was Mr. Hardcore in the full year he was trapped in Purgatory, making it a case of the monsters being trapped there with him rather than the other way round. This is why we can’t choose just the one kill, as Dean was so visceral in his killings in this realm.
He would leave no stone unturned when questioning the monsters, and there was absolutely no mercy in him either, with the monster brutally meeting his end in the next moment. The first instance we saw was enough, where Dean jumped a vampire and sliced his head off with one clean blow; not to mention all those leviathans he decapitated left and right.
Dick Roman
The leviathans had sadly turned out to be rather meek villains in terms of power and could easily be decapitated. The one exception was their leader, defeating whom took the bone of a righteous mortal washed in blood of the fallen. The boys got the tools ready =to set this up, culminating in Dean meeting Dick Roman head on.
His total lack of fear in getting in the face of a monster known for chomping people for fun was what made it so cool, and Dean topped it off by pulling the weapon out and slamming it right in the side of Dick’s throat. Roman exploding and taking Dean away into Purgatory somehow only made the kill even cooler.
Abaddon
The fans wanted Abaddon to die the moment she first showed up, and after antagonizing our heroes for over a year, she was finally put down by Dean Winchester. By this point, he had been imbued by the Mark of Cain, and his thirst for blood knew no bounds.
The best part, though, was how Dean showed telekinesis abilities and summoned the First Blade, before defying Abaddon’s powers to reach out and stab her hard to her death. Dean was so violent in his kill that he ended up lifting Abaddon in the air, and then destroying her corpse in fury.
Styne Family
Kills don’t get much more cathartic than this one, as Dean would mow down the entire Styne family in order to gain revenge for the death of Charlie. Dean was originally held captive by the bad guys, but would break his restraints and spell the beginning of the end.
It was even a little hard to watch in certain moments, thanks to Dean’s absolute vengeance coursing through the scene as he desecrated the bad guys to an extreme extent. He didn’t leave any prisoners either, with a young Styne family member begging for mercy, only for Dean to put him down with zero remorse. It was unnecessary, but the Styne family got what was coming to them.
Azazel
Back in 2007, fans couldn’t have imagined a bigger kill than the one Dean completed by killing Yellow-Eyes, who was later revealed to be the Prince of Hell called Azazel. The Winchesters were out of their element here for sure, but an assist by the ghost of their father ensured Dean got his opening.
It was here that Dean, bloody and battered, took hold of the Colt and shot it through Azazel’s heart with piercing venom. It took a few seconds for the kill to set in, but Dean had no doubt he had finally gotten the demon he had been hunting for almost twenty-five years.
Death
Killing Death sounds like a title for a bad short story, but that is something Dean achieved as he used Death’s own weapon to put him down. Previously, Death had been in a position where he was forcing Dean to take Sam’s life using the Horseman’s own scythe, but Dean’s innate love for Sam eventually pulled through.
Swinging round in such sudden motion it even took Death by surprise, Dean would turn the being who was supposed to be the most powerful in the universe into ash. Death could do nothing other than give a look of utter bewilderment, before crumbling to his end. It was clear that nothing in the universe could usurp Dean’s love for Sammy.
Ruby
Dean had his hands itching to finish off Ruby for two years before he finally got the chance to do so in the Season 4 finale. It was all for naught, though, since Ruby had ensured that Lucifer would break free from the cage; Dean, being a man of short-term goals, decided his mission in that moment was to kill Ruby.
And kill he did, with Dean driving Ruby’s own blade clean into her torso with a little assist from his little brother. It was a simple kill, but making it epic was the fact that Dean still saw consolation from getting some payback rather than rue over Lucifer’s escape. It was basically a stab from the fanbase to Ruby for betraying our trust.
Lucifer
Of course, Dean finally did get around to killing Lucifer himself eventually, with the fight being a total joke. Yes, the fight wasn’t even remotely cool, as the two characters jumped around like clowns, tossing each other around in midair. However, making this a great kill is the replay value behind it.
It’s so lame that you just want to go back and have a good laugh, eventually turning it into a “so bad it’s good” scene. Plus, we have to admit that Lucifer’s death moment did have some pretty rad effects attached to it, as Dean saw his chance and drove the angel blade into the devil, causing the latter to go up in explosive flames before succumbing.
Zachariah
All of us wanted to reach into our screens and give Zachariah a smack in the face after he’d been antagonizing the Winchesters for so long. We finally got our big moment when Dean tore through Zachariah’s skull with an angel blade and ended the latter’s threat.
The set up was awesome too, with Dean taunting he’d get Michael to incinerate Zachariah. After luring the angel to get into his face in rage, Dean took out a smartly concealed blade and proclaimed he would be the one to kill Zachariah once and for all, before stabbing the antagonist right in the skull. It didn’t hurt that the effects and music were equally as cool.