'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.



'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.


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 (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.

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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