Hero Gets the Girl, Monster Gets the Gank: Team Free Will’s Gnarliest Kills on ‘Supernatural’

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Contributors: Kenedi, Jules

Saving people, hunting things — the family business. Supernatural‘s hunters have been the knights in shining armor — er, flannel — for many victims of the things that go bump in the night over the years. Often a thankless job with no money and no fame, day in and day out, these gruff and grizzly hunters put their lives on the line to save people from the fates that often befell them and their loved ones. No one can attest to this more than Team Free Will.

Putting aside their chances at a normal, apple pie (read happy) life in order to keep the world safe over and over again, no one was more dedicated to — or better at — their jobs than TFW. This fact was repeatedly demonstrated by the plethora of truly nasty kills that the audience got to witness — seriously, there have been some truly gruesome ganks over the years. To celebrate the legacy of our favorite hunters and their dedication to the life, we present to you TFW’s gnarliest kills on Supernatural.

*WARNING: If gore isn’t for you, turn around now. GIFs of each mentioned scene are included*

“Eat it Twilight”

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This scene is so well done. The contrast of Sam’s new “normal” (short-lived, sorry Sammy) life that’s shown while he cuts lemons in the bar really emphasizes the grittiness of a hunter’s life when Dean is conversely shown sawing off the vamp’s head (the sawing motions, oh my god) — all to the iconic tune of “Simple Man.” While the kill isn’t even explicitly shown, the scene is so artfully put together that the subtext comes together to paint one very … vivid … picture.

Sam Garroting Gordon’s Head Off

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To this day, this is one of the absolute gnarliest kills, if not the singlehanded most gruesome one, on the show. The eye contact, the spurting carotid, Sam literally rubbing his hands raw pulling the wire … whew. Early seasons Supernatural did not hold back. Then again, that’s just Kripke isn’t it? Because this looks like something straight out of The Boys.

The Styne Massacre

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With Dean under the influence of the mark, this was one of the more … gruesome things that he did — and while terrible, we can’t exactly say we were sad to see the Stynes go, especially after what they did to our girl Charlie. The hardest part to accept about this, the thing that made it as stomach-churning as it was, was Dean’s absolute lack of empathy or remorse, especially when killing the innocent Cy Styne. His eyes? Blank. Absolutely blank. This is the mark on a quest for blood, and blood only.

Castiel Says Heads Will Roll

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Like we said, this angel’s got an instinct for drama. When Bobby’s interrogation of a Jefferson Starship isn’t gathering the intelligence they need Castiel offers his interrogation services. As Bobby waits outside, Cas gets the address where Eve is located and promptly rips the monster’s head off with his bare hands. We don’t even see the kill happen, but Bobby’s disturbed reaction combined with Castiel’s refusal to look him in the eye as he wipes the blood from his hands takes the emotional tension to a high level. Early season Castiel was a terrifying killer, and it’s episodes like “Mommy Dearest” that remind the viewer of his strength.

Sam Killing Alastair

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Let’s be honest, no one was sorry to see Alastair go. Between his role in transforming Dean into a torturer in Hell and his generally creepy demeanor, Alastair was a memorable villain (perhaps one of the series’ best). But his death also marked an important and frightening development for Sam’s experimentation with demon blood as he used his new powers to kill Alastair, which caused even battle hardened Castiel to pause as he witnessed it. The look of shock on Alastair’s face as he died combined with the utterly terrifying anger on Sam’s make Alastair’s death one of the most disturbing on the show.

“Heil This”

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This one isn’t even particularly gruesome, it’s just so freaking memorable — I mean come on, he killed Hitler. The patented Winchester sass shines through as Dean once again shows us why he’s an icon and ices Der Führer himself with some sarcastic parting words. Enough said.

The Infamous Knife Throw

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I mean … he tried to warn him. Sometimes you forget that Castiel isn’t just some nerdy little angel dude, but then he goes and logs a kill like this. The execution of this skill? Immaculate. Despite his awkwardly adorkable demeanor, Cas was a soldier, and everyone would do best not to forget that.

Dean and Sam Kill Ruby

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Ruby’s betrayal in season 4 came as a shock to viewers (and to Sam). After getting in one of the best villain exit lines ever (“I’m … I’m awesome!”), Ruby met her end with Sam holding her as Dean twisted the knife. Making this moment even more memorable is the fact that Ruby is played by Jared Padalecki’s wife Genevieve Padalecki (then Genevieve Cortese), who even appears as herself in season 6’s “The French Mistake”. Aside from being a future traumatic memory for the Padalecki children, Ruby’s death at the hands of both Winchesters is iconic and, dare we say, awesome.

Castiel Takes an Eye For an Eye-on

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Castiel kills are always … a little extra. This angel has a flair for the dramatic, going all in on every kill. Nowhere is this more apparent than in season 8’s “The Great Escapist” when Castiel kills Ion by digging the Angel Bullet out of his gut (!!) and shoving it through Ion’s eye. Cas might be a baby in a trench coat on occasion, but he has the killer instincts of a soldier and an excellent sense of poetic justice.

Yellow Eyes Meets His End

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It’s the moment Supernatural had been building towards ever since Dad went on a hunting trip and didn’t come back. The Winchesters found themselves face to face with Yellow Eyes himself, the demon responsible for so many of the terrible things that had happened to the family so far. Dean has one opportunity to exact revenge on Azazel and he doesn’t miss, finally destroying the demon once and for all. It’s a beautifully shot moment as the kill itself happens in almost complete silence, with Azazel’s eyes slowly turning blue as the life drains from his body. This may not be one of the most ghastly kills on Supernatural, but it’s an emotionally resonant one for Dean and Sam.

Bonus Round

Bobby Stabbing a Demon … and Himself

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Sometimes you have to take matters into your own hands, and sometimes that includes stabbing yourself to rid your body of the demon inhabiting it.

Jack vs. Michael

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It’s sweet that Jack finally calls himself a Winchester and a hunter before immediately absorbing (eating?) Michael in a terrifying display of his powers. As Jack says, he’s not a child.

Woodchipper Beats Everything

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Rufus wasn’t kidding when he said “Woodchipper, that-that pretty much trumps … everything.”

These spine-chilling kills, along with the many, many others that have occurred over the years, showcase TFW’s undeniable skills. However, it must be said that the thing that made this group of salty old hunters some of the best the world had ever seen wasn’t their weapons and combat prowess (though that never hurts), it was their dedication not only to the job but to putting things right, to making the world a safer place, and especially to the people they saved.

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By Kenedi
Kenedi is a college student with her sights set on attending medical school. When she isn't hard at work, Kenedi enjoys reading, watching her favorite shows, and listening to music. Some of her favorite fandoms include Supernatural, One Tree Hill, Bones, Abbott Elementary, Percy Jackson, and Scrubs.
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