'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters

In honor of the CW's Supernatural's landmark 300th episode "Lebanon," we're here to highlight the 10 most influential characters from throughout the entire series run. Fellow Bleeding Cool contributor Tom Chang and I carefully narrowed down the list, casting a spotlight on the SPN Family's most beloved–and delightfully hateable–personalities. We couldn't bring ourselves to rank them…so we'll introduce them chronologically, instead.

SEVERAL SEASONS WORTH OF SPOILERS AHEAD!

https://www.youtube.com/watch?v=lNSoK7vULZI

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural –"All Along the Watchtower" — SN1223c_0066 .jpg — Pictured: Samantha Smith as Mary Winchester — Photo: Dean Buscher/The CW — © 2017 The CW Network, LLC. All Rights Reserved

Mary Winchester

The Winchester matriarch is the reason why John raised his boys to be hunters. Their goal was to catch the demon that killed her. Once they did that, the boys moved onto saving the world. Our perception of Mary (Samantha Smith) has changed over the years–mother, wife, hunter, Death defier, and soul searcher. Flashbacks revealed how Mary was raised to be a hunter, but her priorities changed when she met John. She made a deal with Azazel (the Yellow-Eyed Demon) to save John's life. She stopped hunting, got married, and had a family. Just when life was at its sweetest, Azazel came to collect.

We never imagined that years later, Chuck and Amara would reward the Winchester Brothers by resurrecting their beloved mom. Unfortunately, Mary was fine resting in peace and it takes her a couple of years adjusting to this life. Now she has found a new sense of purpose, hunting alongside her boys. In episode 300, we see Mary's vulnerability when she briefly reunites with John.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
"In My Time of Dying" — (L-R) Pictured Jeffrey Dean Morgan as John Winchester and Jensen Ackles as Dean Winchester SUPERNATURAL on The CW Photo: David Gray/The CW2006 The CW Network LLC. All Rights Reserved.

John Winchester

John (Jeffrey Dean Morgan) was not a perfect father to Sam and Dean, but he did love them and tried his best. He knew nothing about the supernatural until Azazel brutally murdered Mary before his eyes. From that moment on, John's purpose in life was to track down the Yellow-Eyed Demon. Embarking on this vengeful crusade turned him into a renowned hunter. Sam and Dean's reputation was preceded by their Winchester name and the legacy John set.

In the Season 2 premiere, John makes a deal with Azazel to save Dean's life. He gives Dean a sense of closure and leaves him with a haunting message. But poor Sammy never got to say goodbye and felt guilty for spending so much time fighting with his dad. In "Lebanon," John and Sam finally have a heartwarming conversation that's been twelve years in the making. He makes his peace and finally has proper goodbyes with everyone he loves.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
"How to Win Friends and Influence Monsters" – (L-R): Jared Padalecki as Sam, Jim Beaver as Bobby, and Jensen Ackles as Dean in SUPERNATURAL on The CW. Photo: Jack Rowand/The CW©2011 The CW Network, LLC. All Rights Reserved.

Bobby

Named from the show's producer, Robert Singer, Bobby (Jim Beaver) became a strong staple of Supernatural's early seasons. Filling the void left behind by John, Bobby became Sam and Dean's surrogate father to help guide them to become better hunters, while the brothers fulfilled the void left behind by his deceased son. Bobby took a more auxiliary role in later seasons, helping the Winchesters through cases as a third wheel. Ultimately, Bobby sacrificed himself for the boys in Season Eight. The affectionate "idjit" made sporadic and moving appearances through Season 11 when his soul eventually ascended into heaven.

We do meet alternate Bobby when the Winchesters crossed dimensions to save Jack and Mary in Season 12. Alternate Bobby has the same characteristics as the original–losing his son and surviving the apocalypse. With Castiel firmly in the group as the clear no. 3 and Jack tagging along, Bobby's become far more a background character as a refugee from the alternate world. He also shares a different kind of chemistry with Mary, although we haven't seen anything go down–they alluded to flirtation on more than one occasion.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural/The CW

Azazel (aka the Yellow-Eyed Demon)

Azazel (Fredric Lehne) is the catalyst that launched the Winchester men into the family business–saving people, hunting things. Sure they ganked a bunch of baddies along the way, but Yellow-Eyes was their first endgame. He sure was fun to hate. Although Azazel took turns possessing different meat-suits (including John and Mary), Lehne really made a meal out of this villainous role.

Yellow-Eyes evaded the Winchesters for 20 years. When John finally came face-to-face with his wife's killer, he traded revenge for Dean's life. After John's death, the boys discovered that Azazel bestowed Sam with an unwanted gift. The Prince of Hell created "special children" with various powers. His goal was to find the perfect vessel for Lucifer. In the epic Season 2 finale, "All Hell Breaks Loose Part 1 and 2," he pits those children against each other to see who survives. Sam shockingly dies, but Dean makes a deal to resurrect him.

Ultimately, Dean kills Azazel with the help of John's spirit. However, before bitting the Colt's bullet, Yellow-Eyes successfully unleashed countless demons from the Gates of Hell. Years after his demise, this demon continued to haunt Sam and Dean. He made a lasting impression on the Winchesters and the SPN Family.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural – Image: SN09_MONDO_NM_ Misha.0001 – Pictured: Misha Collins as Castiel — Credit: Nino Mu–oz /The CW — © 2013 The CW Network. All Rights Reserved

Castiel

Castiel (Misha Collins) is the only non-Winchester Supernatural character to last over 100 episodes. Until newcomer Jack, Cass was the Winchesters' most powerful ally as an angel with healing powers, enhanced strength, and mental abilities thanks to his grace. Like the Winchesters, Cass fought on both sides of the good-evil spectrum. Collins' deadpan delivery and his initial child-like wonder made the character loveable. He gripped Dean tight and raised from perdition the two soon struck-up a fan-favorite bromance. In recent seasons, he's become Jack's surrogate father teaching him how to use his powers to help people and adjust to life as a benevolent Nephalem.

The show explores many different aspects of Cass' life, similar to how it depicts the Winchester family history. We see him struggle with taking permanent control of his vessel, Jimmy. A once-estranged daughter, Claire (Kathryn Love Newton) rejected everything Cass came to be, especially after taking Jimmy away from her. Ironically, years later, Claire is inspired by the Winchesters and embarks on a life of hunting.

In Episode 300, we see what would have become of Castiel if he never bonded with the Winchesters. Let's just say the boys make Cass is a better angel and person.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural — "Devil's Bargain" — Image Number: SN1313b_0283b.jpg — Pictured: Mark Pellegrino as Lucifer — Photo: Dean Buscher/The CW — © 2018 The CW Network, LLC All Rights Reserved

Lucifer

Lucifer (Mark Pellegrino) has been a thorn at the Winchester's side. Always a constant threat, he never hides his megalomaniac intentions and cruel nature. Playing Lucifer in any fictional work can be difficult when channeling who and what he is. He is more than a powerful threat with a short temper that levels anything in a moment's notice. The real danger comes from his charm and manipulative nature that he gleefully exudes from any vessel – even Sam, Cass and Rick Springfield. The Winchesters managed to lock him in a cage for a while, but he eventually got out. During that time he spawned a Nephilim- Jack (Alexander Calvert)–and smarmily sought to reclaim his throne as the King of Hell, which Crowley occupied in his absence.

In Season 14, Lucifer was purged from his longtime vessel Nick during a climactic fight with Dean (who was possessed and enhanced with Michael's powers). It's a testament to creator Eric Kripke and the writing to explore another side of the character we never have seen before.

The show seldom visits the lives of the vessels angels and demons come to possess. While there was much sadness attached to the chaos Cass brought to Jimmy's life, we saw Lucifer vessel "relearning" how to be human again and feeling more vulnerable than ever before. What's shocking is how much Lucifer actually kept Nick composed. We recently discovered how Luci's presence poisoned Nick's compromisable soul, launching him into a psychotic rage in his search for vengeance. It's a testament to Pellegrino's dynamic performance–he's arguably among the best to ever play the Devil Incarnate.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural – Image: SN09_MONDO_NM_Mark.0001 – Pictured: Mark Sheppard as Crowley — Credit: Nino Mu–oz /The CW — © 2013 The CW Network. All Rights Reserved

Crowley

Crowley (Mark Sheppard) is perhaps the Winchesters' favorite frienemy. The King of Hell, a title he's had to reclaim more than once, was a force to reckon with until he found himself helping his nemeses far more than he wanted to for the greater good. As if dealing with those who constantly foil his plans aren't enough, he also had to contend with his overbearing mother, Rowena (Ruth Connell), a witch who always callously calls him "Fergus." After learning how she mistreated him as a child, we kind of developed a soft spot for the sharp-tongued demon with a conscience.

During his final years on the show, Sheppard was promoted to series regular. With one eye looking at the brothers and the other searching for greater power and omnipotence, the jig was finally up at the end of Season 12 when he selflessly helped the Winchesters one last time before sacrificing himself at the end of an angel dagger. While Sheppard swore not to come back to the show, we're hoping he'll reprise the role at some point. His absence is felt in "Lebanon."

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural — "The Big Empty" — Image Number: SN1304a_0230ra.jpg — Pictured (L-R): Alexander Calvert as Jack, Jared Padalecki as Sam and Jensen Ackles as Dean — Photo: Jack Rowand/The CW — © 2017 The CW Network, LLC All Rights Reserved.

Jack

In Supernatural's recent years, the creative process seemed to run on fumes becoming predictable and uninspired. That is until Jack (Alexander Calvert) came into the Winchester's lives. As the son of Lucifer and Kelly, his human mother Dean was convinced a Nephalem like Jack would turn on them–setting the world ablaze unless he is stopped.

Upon discovering his own nature, Jack set out to change his fate and how the world perceives him. Despite his quick growth, Jack struggled to adjust to the world around him. He possessed two traits which Sam always held out hope for in everyone: remorse and compassion. Jack's efforts even won over distrustful Dean. He became part of the family he always longed for, even going above and beyond in self-sacrifice.

Despite his omnipotence, he still exhibits a childlike innocence, which is the kind of character the show needed. He reminds us of Castiel in many ways (not just in appearance and mannerism). Jack may have adjusted to life on earth, but he's one of a very few enhanced beings who wish to make a better world from ongoing threats–just like Cass.

'Supernatural' @ 300: Our 10 Most Beloved (and Delightfully Hated) Characters
Supernatural — "Exodus" — Image Number: SN1322a_0107b.jpg — Pictured (L-R): Richard Speight Jr. as Gabriel, Alexander Calvert as Jack and Mark Pellegrino as Lucifer — Photo: Robert Falconer/The CW — © 2018 The CW Network, LLC All Rights Reserved

Gabriel the Trickster/Archangel

We can never count Gabriel (Richard Speight Jr.) out. This trickster made an unforgettable entrance in Season 1 when he mischievously brought urban legends to life in "Tall Tales." He's been toying with the boys ever since, but there's always a method to his madness.

In Season 5, we discover that Gabriel is an archangel masquerading as his buddy Loki (a demi-god trickster). He uses his entertaining powers to teach the Winchesters lessons, oftentimes making us laugh and cry within the same moment. He hilariously killed Dean on loop in "Mystery Spot," cleverly used "Changing Channels" to force the boys to play their part in the Apocalypse, faked his death in a duke out with his brother Lucifer, and then paid the price when Asmodeus held him in captivity and slowly siphoned his grace.

Ultimately, Gabriel meets the same fate many Winchester loyalists find. He sacrifices himself helping the boys save Mary and Jack from Apocalypse World. He dies at the hands of Alternate Michael in Season 13. Given the infectious playfulness Speight brings to the role, we really another miracle bring Gabriel back.

supernatural 300 10 characters
Supernatural — "Wayward Sisters" — Image Number: SN1310a_0225b.jpg — Pictured (L-R): Kathryn Newton as Claire, Katherine Ramdeen as Alex, Kim Rhodes as Jody Mills, Briana Buckmaster as Donna and Clark Backo as Patience — Photo: Dean Buscher/The CW — © 2017 The CW Network, LLC All Rights Reserved

Wayward Sisters

Ladies just can't catch a break on Supernatural. They are always dying, no matter how badass they are. In Season 2, we fell for the mother-daughter duo: Ellen (Samantha Ferris) and Jo Harvelle (Alona Tal). Their Roadhouse Family showed up for Sam and Dean in the wake of John's death. In Season 7, spunky hacker Charlie (Felicia Day) rocked the Supernatural scene and became another cool role model to female fans. Sadly, they all lost their lives in battle.

We met Sheriff Jody Mills (Kim Rhodes) through Bobby in Season 5 and we feared we'd lose her too. Luckily, she's still around. Over the past few years, she's adopted and trained a group of young female hunters, including Claire (Kathryn Newton). With fellow Sheriff Donna (Briana Buckmaster) as her diplomatic wing woman, the Wayward Sisters are a force to be reckoned with. They've even saved Sam and Dean on a few occasions. Which is why the Winchester Brothers know their Supernatural Sisters are just a phone call away.

Of course, we have to give honorable mentions to characters like Chuck (Rob Benedict), Garth (DJ Qualls), Zachariah (Kurt Fuller), Cain (Timothy Omundson), and Abaddon (Alaina Huffman).  They've left a lasting impression on fans and changed the road the Winchesters were set on.  

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Supernatural has accumulated so many incredible characters over the years, some of whom we never could have imagined into existence. The longevity of this series is in its creativity and self-awareness. This show knows its audience and caters to it. They take accountability for missteps and try learning from them, yet the writers never shy away from taking wild risks. Anything is truly possible on this show and that's why we're celebrating its 300th episode.

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About Tiffany Tchobanian

I'm a Bay Area-based freelance journalist and content creator with an insatiable passion for TV, film, and pop-culture. When I'm not watching TV, I'm talking about it...
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