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10. Pagan Gods in Season 3’s “A Very Supernatural Christmas”
At the most recent “Salute to Supernatural” convention in Burbank, California a fan asked Jared Padalecki and Jensen Ackles what they thought their characters would ask Santa for—to which Padalecki replied, “Didn’t we kill him?” Well, not exactly but in the opening moments of their special holiday episode it certainly seemed like they were going to. Instead, though, it turned out that the Meadowsweet wreath making Carrigans (Merrilyn Gann and Spencer Garrett) were actually Pagan Gods who were completing their annual ritual sacrifice. While they first tied the boys up, draining some of their blood and almost extracting one of Dean’s teeth, ultimately the Winchesters prevailed and took them down—by staking them with Christmas tree branches, no less! What made this even more memorable was that it was during what was supposed to be Dean’s last year. Many people would just want to spend their last Christmas in front of a fire with family, but not these boys!
9. Emma in Season 7’s “The Slice Girls”
Sam Winchester killed his brother’s daughter. Yes, it sounded weird to us at the time, too, but then again out of all the one-night stands Dean has had, maybe the truly weird thing is that only one resulted in an offspring. Anyway, after picking up an Amazon in a bar, she gave birth to a rapidly growing daughter named Emma (Alexia Fast), who tracked down her dad and tried to play on his emotions by pretending she didn’t want to succumb to her nature. So, the usually “shoot first, ask questions later” kind of guy Dean hesitated here– and his little brother stepped in to finish the job.
8. Madison in Season 2’s “Heart”
Recently Jared Padalecki was asked how he most differs from his character of Sam Winchester, and he replied that he has never killed anyone he has dated. While his character has felt responsible for his college sweetheart’s death, the one who died at his hand was arguably more memorable because it came at a moment in the series, and in Sam’s life, when he realized just how unlikely it was that a normal life was possible for him. Madison (Emmanuelle Vaugier) was a woman he met while hunting a werewolf, and sensing his chemistry with her, big brother Dean stepped back and let Sammy stand guard over her. Only, Madison had already been bitten, too, and when an attempt to cure her failed, Sam killed her so she wouldn’t have to live as a monster or hurt any innocent people.
7. Gordon Walker in Season 3’s “Fresh Blood”
The Winchester brothers had a tumultuous relationship with Gordon (Sterling K. Brown) at best. He was a vampire hunter who saw all of them as the sample: evil “things” that had to be put down. When he learned Sam was going to be used by a demon in an army of evil, he began to hunt the younger Winchester, too. Ironically, Gordon ended up getting turned into a vampire, which not only made him the thing he hated most but also gave the show a way to have the Winchesters kill him and call it “all in a day’s work.” The face-off was Gordon and Sam for this kill, with Gordon planning to take out Sam and then off himself, but in one of the first showings of Sam’s brute force of strength, he managed not only to get the upper-hand but to behead Gordon by garroting him with wire.
6. Abaddon in Season 9’s “King of the Damned”
There was a campaign going on for the new king (or queen) of Hell, and for awhile there it looked like Abaddon (Alaina Huffman) might come out on top because Crowley (Mark Sheppard) had been recently saddled with some more human emotions. But what she didn’t count on was that Crowley and the Winchesters were working together—at least momentarily—to take down the common enemy: her. Crowley told the boys where they could find the First Blade—the only weapon that could strike down a Knight of Hell— he had hidden. Armed with that, and aided by the extra strength and telekinetic ability the Mark of Cain granted him, Dean was able to overpower Abaddon and kill her. The effects of that kill were felt for many episodes that followed—by Sam, worried about what the kill did to his brother; by Dean, who also couldn’t ignore what was newly coursing through him; and by the audience, who lost a fan favorite villain.
5. Benny in Season 8’s “Taxi Driver”
It was only a matter of time from the eighth season premiere when the vampire Benny (Ty Olsson) hitched a ride back from Purgatory with Dean that he’d have to be sent back. Though Benny promised Dean he wouldn’t resort to his old ways, his adaptation to the modern world was a struggle to say the least. It didn’t help that he was hunted by someone who didn’t believe he could change, nor that he found slipping into old patterns was easier than he would have liked. Benny was like a guy who had been released from prison, only to find he missed the comfortable ease of life on the inside. So when Dean called upon his brother in arms for a favor that required him killing Benny in order to return to Purgatory, Benny quickly agreed. The sacrifice was great—both on Benny’s side and on Dean’s, as he had to put down someone he saw as a brother and a friend.
4. Lilith in Season 4’s “Lucifer Rising”
Poor Sam. He has racked up such a high body count, and every now and then he gets one wrong. It’s hard to fault him for Lilith (Katherine Boecher), though; for two seasons she seemed to be an even bigger bad than Azazel (Fredic Lehne) had been, and she had to be stopped. Sam used his new demon blood fueled powers on her, and as her blood pooled on the floor of the chapel they were standing in, it began to fill the cracks. Her death was the final seal needed to set Lucifer free, so while it may have been one of the simpler kills stunt-wise, it had one of the greatest impacts on the show’s mythology.
3. Ruby in Season 4’s “Lucifer Rising”
Ruby (Genevieve Cortese) had been palling around with Sam all season long, teaching him to tap into his powers, feeding him demon blood to make him stronger so he could kill Lilith, who was trying to set Lucifer free. In the fourth season finale, right after Sam actually succeeded in that kill (see #4), Ruby revealed that she had been manipulating him for the demonic cause all along. Fueled by betrayal Sam holds her as Dean stabs her with her own knife. It is one of the strongest instances of the brothers working together to take down a force of evil.
2. Zachariah in Season 5’s “Point of No Return”
As show creator Eric Kripke’s run as showrunner came to a close, #TeamFreeWill became one of the hottest themes and discussion topics. The apocalypse was nearing, with the Winchesters seemingly destined to end up on opposite sides. Lucifer (Mark Pellegrino) was trying to get Sam to accept him in, and arcangel Zachariah (Kurt Fuller) was trying to convince Dean to say “yes” to accepting Michael in through coercion or sheer force. But Dean was able to distract Zachariah by saying he would agree if Michael would kill Zachariah—because who did he think was more important to Michael between the two of them? This spoke directly to the arcangel’s fears as well as pride, and Dean was able to fatally stab him in the jaw.
1. Azazel aka Yellow-Eyed Demon in Season 2’s “All Hell Breaks Loose”
Supernatural started out as a monster of the week show, with two brothers and a bad-ass muscle car traveling the country, saving people and hunting things. It wasn’t until the second season that the show really started to dive deeper into a demonic mythology. Azazel aka the Yellow-Eyed Demon (Fredric Lehne) was the thing that killed Sam and Dean’s mother; he was the thing that stood over Sam’s crib and dripped blood into his mouth, turning him into one of his future soldiers; he was the reason the Devil’s Gate opened; and he was the reason, ultimately, that Dean sold his soul to bring his brother back to life. But if Dean thought he was going to die, at least he got to go out knowing he took down the thing that ruined his family. No Supernatural fan will ever forget the moment Dean fired the Colt directly into Azazel’s heart. It was a moment that put all of the boys’ previous kills into perspective and was the first major triumph in the grand scheme of mythology.
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