Throughout 15 seasons of Supernatural, the brothers Sam and Dean Winchester have bested countless bad guys.
Some they sent packing in one episode. Others like Meg, Crowley, and Rowena stayed long enough to turn good and help Sam, Dean, and Castiel against worse evil. And then there were good guys, like God, that turned hostile and had to be dealt with.
It’s hard to rank 15 years’ worth of villains on a list. But we can still pick some of the most noteworthy baddies of the show and score them, right? So we’re skipping episodic villains and focusing on those around for more episodes to make us hate them.
20. British Men of Letters
The British chapter of the Men of Letters sounded intriguing but didn’t translate well on screen. It was hard to warm up to Lady Bevell (Elizabeth Blackmore), who tortured Sam Winchester, or to Mick (Adam Fergus) and Ketch (David Haydn-Jones), who helped deceive Dean, even if they eventually died helping our boys.
19. Humans
Dean Winchester was right. Monsters, you can understand. But humans were the worst! Every time Supernatural showed us the horror humans could inflict on others—like “The Benders” in season 1—sometimes even their flesh and blood—like in “American Nightmare” in season 12—you shuddered and agreed with Dean.
18. Gordon Walker
Emmy and Golden Globe winner and Oscar nominee Sterling K. Brown, who played Gordon Walker, first appeared in season 2’s “Bloodlust,” as a hunter who befriends Dean. Ellen describes him as “a skilled hunter in the sense that Hannibal Lecter is a good psychiatrist.” Walker becomes an enemy who attempts to kill Sam repeatedly. He appears in four episodes, ultimately gets turned into a vampire, and is decapitated and killed by Sam.
17. Eve and her son, the Alpha Vampire
Supernatural may not let its female characters stay on for long, but they sure as hell are fascinating creatures. Eve (Julia Maxwell), the one who birthed all supernatural beings and is addressed as ‘Mother’, starts off as the chief antagonist of Supernatural season 6. The scene where she appears as Mary Winchester (Samantha Smith) to Dean and he manages to kill her by spiking his blood is an epic twist! Of her many children, Rick Worthy’s Alpha Vampire made for a formidable figure during the season and in later episodes.
16. Michael (Apocalypse World)
Michael from the Apocalypse World is slightly more terrifying than his previous iterations because he is played by Christian Keyes, who doesn’t play any other character. Michael doesn’t get much to do when he finally gets Dean as a vessel, which is good for seeing Jensen Ackles play a cold, calculated antagonist dressed in slick period outfits, but nothing more.
15. Amara / The Darkness
Samantha Isler and Emily Swallow’s Amara a.k.a. The Darkness a.k.a. God’s angry older sister, and her mysterious connection to Dean made for an interesting villain dynamic powering season 11. She eventually turns an ally and even helps the Winchesters against her brother in the final season.
14. Asmodeus
The youngest and weakest Prince of Hell, Jeffrey Vincent Parise’s all-white-clad villain Asmodeus from season 13 was stylish and entertaining and left an impression despite his short screen time. Of course, we hate him for what he did to Gabriel, but the scene where Gabriel returns to archangel form and decimates Asmodeus is one for the books!
13. Naomi
This angel, who was wiling to cross limits for the greater good of Heaven, is much hated. Naomi (Amanda Tapping) returned Castiel from Purgatory (thanks) and reprogrammed him to kill Dean (no thanks!)! Almost killed by Metatron, eventually, Naomi became an ally to Castiel in Heaven. Interestingly, she was imprisoned in Heaven’s dungeons by Dumah, but we never find out what happens to her after Jack becomes God.
12. Ruby
It’s fun knowing that IRL, Jared Padalecki and Genevieve Cortese, a.k.a. Sam and the demon Ruby, ended up together because that chemistry was so hot! Since her first appearance in the season 3 premiere “The Magnificent Seven” when Katie Cassidy played her, Ruby and her demon-killing knife were fascinating. Her gently nudging Sam’s demon-blood addiction, and ultimate revelation as Lucifer’s most loyal servant was great writing. Her death scene, with Sam holding her hands behind as Dean stabbed her with her knife in the season 4 finale, “Lucifer Rising,” was great television!
11. Lilith
Lilith made a fantastic debut (played by Rachel Pattee) in season 3’s “Jus In Bello” when she killed FBI Agent Henrikson and others. She holds the crossroads deal that puts Dean in Hell, takes over the body of a little girl (Sierra McCormick) to hold an entire town hostage, and has a complicated love for Lucifer as his first demon, for whom she willingly sacrifices her life. Lilith (Katherine Boecher) was portrayed rather well, right up to season 15 when God himself resurrects her to do his dirty work, and she is ultimately killed by the archangel Michael.
10. Dick Roman / Leviathans
Okay, sure season 7 was a hit and a miss in many ways, but the Leviathans and particularly James Patrick Stuart as Dick Roman were just such frustratingly good villains. We lost Bobby because of them!
9. Meg Masters
Meg is just a legend, from when she was portrayed by Nicki Aycox who called Azazel her daddy, right up to Rachel Miner’s Meg who looked after Castiel and sacrificed herself to Crowley, giving the Winchesters and Cas a chance to escape with the Word of God tablet. Her little joke of calling Castiel “Clarence” and their “I learnt it from the pizza man” kiss is one of the best and sexiest Castiel scenes!
8. God
Making God an absentee father, an insecure brother, and a writer with hubris and having him turn the ultimate villain to the free will we humans think we have was perhaps one of the best Supernatural villain arcs. I enjoyed all the meta episodes that featured Rob Benedict as Chuck/God, especially season 4’s “The Monster at the End of This Book,” and season 11’s “Don’t Call Me Shurley” where Metatron becomes his editor and calls God out on his BS and Rob Benedict sings!
7. Abaddon
Alaina Huffman’s Prince of Hell, Abaddon, with her disgust of Crowley as the ruler of Hell, had so much spunk! Yet another redhead female character on Supernatural that had an epic life but an even more epic death. That scene from the season 9 episode “King of the Damned” when Dean slays Abaddon with the First Blade is jaw-dropping!
6. Rowena
Another redhead with spunk, the witch Rowena, played by Ruth Connell, will always be Brat. Her complicated relationship with Crowley and Sam Winchester and her gradual turn to the good that made her one of the best rulers of Hell was fulfilling to watch. Her accent and glorious eye-makeup looks will always be iconic!
5. Alastair
Mark Rolston and Christopher Heyerdahl’s chilling portrayal of the old, powerful, sadistic demon Alastair, who tortured Dean in Hell and then promoted him, is one of the best demons in all 15 seasons of Supernatural! The scene where Dean tortures Alastair in season 4’s “On The Head of a Pin” (one of the best episodes of the series) is unforgettable because of Heyerdahl’s and Jensen Ackles’ performances!
4. Azazel
Fredric Lehne’s portrayal of Prince of Hell Azazel a.k.a. Yellow-eyed demon that killed John and Mary Winchester was phenomenal! Back when Supernatural had just begun, Azazel’s yellow eyes as he burnt Mary Winchester on the ceiling over baby Sam’s crib was the vision that haunted us all. His death at the hands of Dean in season 2, “All Hell Breaks Loose Part 2,” helped by the ghost of John of course, was rather cinematic!
3. Metatron
Curtis Armstrong’s Metatron is easily the most hated Supernatural villain. This “nebbishy” little Scribe of God was so diabolical that he managed to single-handedly destroy the lives of all our favourite boys—Sam (via Gadreel), Dean, Castiel, and Kevin Tran! But he gave us two of the best season finales in season 8 “Sacrifice’, by shutting the gates of Heaven and making every angel fall to earth, and season 9, when he killed Dean and we got Demon Dean!
2. Lucifer
Mark Pellegrino’s Lucifer is hands down the best portrayal of Satan we’ve seen on television. Season 5 remains one of the best Supernatural season, and Lucifer’s villain energy is chef’s kiss. In season 7 when he tortures Sam in his mind or when he tries to be the new God and a father to Jack in season 13 brings out so many facets of this complicated fallen angel who used to be God’s favourite son.
1. Crowley
Hello, boys! Who else did you think would be on top but the King of Hell and the one who always survives, Fergus McCloud a.k.a. Crowley! A human who sold his soul to get a few extra inches to his willy and went from becoming a crossroads demon to the King of Hell to Dean Winchester’s boyfriend, and a war-time hero (he sacrificed himself to save them!)? Now that’s a true underdog story if there ever was one. Mark A. Sheppard deserves all the awards for what he did with Crowley, especially in the season 8 finale, “Sacrifice” when Sam tries to cure him of being a demon. There will never be another Crowley!
Published: Sep 3, 2024 04:26 pm