Rogue angels, uncontrollable demons, and sometimes an angry God, there’s nothing that the Winchester boys haven’t dealt with. Perhaps one of the most popular television sibling duos of all time, Sam and Dean Winchester have been entertaining fans for more than 15 years. One of the longest-running sci-fi/fantasy TV series of all time, CW’s Supernatural has garnered a huge fandom in its fifteen-year successful run. Besides its intriguing and mostly outlandish storyline, one of the things that kept the viewers stuck to the series is its incredibly alluring cast.

From Dean’s lovable bad-boy persona to Crowley’s zesty sarcasm, the TV series has a truck full of memorable characters who have kept the show going. It’s safe to say that every Supernatural character has done justice in portraying their role to elevate the plot, but some have done a better job than others, making them unforgettable.

Jack Kline Was the Little Brother That the Winchesters Needed

  • Jack Kline first appeared in Season 13, Episode 1, “Lost and Found.”
  • He is the only known Nephilim fathered by an Archangel.
  • Jack’s final appearance is in Season 15, Episode 18.

Jack Kline has a complicated origin as a Nephilim with an even more complex destiny. His addition to the series was welcoming, especially to the Winchester brothers’ dynamics. The fandom has been particularly accepting of Jack’s character since he fulfills the role of the little brother who grew the Winchesters’ ever-diminishing family.

Despite Jack being one of the main characters in the show’s last few seasons, he managed to win the fans over with his innocent persona, especially when learning about the ways of life. His role has been instrumental in the final arcs, and every time he goes into his power mode, he simply wows the audience. His boyish charm and the capability of turning every next character into a potential parent are some of the most likable things about Jack.

Rowena MacLeod is a Sneaky Manipulator with Style

  • Rowena first appeared in Season 10, Episode 3.
  • She’s a powerful witch who is extremely hard to kill.
  • Rowena’s final appearance is in Season 15, Episode 3.

Rowena is an enduring character who has proved her worth as a fan favorite ever since her introduction to the series. She’s introduced as a powerful witch and Crowley’s mother, who is always ready to abandon or use him for her own benefit. She may not exactly be the Mother of the Year, but she’s a class manipulator who knows how to work her way around, even in Hell. Like Crowley, she’s also hard to distinguish whether she’s on team Winchester or just backstabbing people for selfish reasons.

Although she loves making a fool out of the Winchesters most of the time, she does become their ally in the end and does her part in saving the world. Rowena’s wit and sassy jokes immediately make her a lovable character, and when it comes to sarcasm, she’s two steps ahead of Crowley.

Lucifer Was One of the Most Entertaining Characters

  • Lucifer first appears in Season 4, Episode 22.
  • The Archangel has taken many hosts throughout his villainous run in the series.
  • Lucifer’s finally bites the dust in Season 15, Episode 19.

It’s commendable how Supernatural never lets its negative characters be one-dimensional or victims of mainstream villainous tropes. For instance, Lucifer was the big bad of the series for quite some time and did a wonderful job at being a snarky yet witty bad guy. He’s the kind of character that fans love to hate but is so entertaining and has a powerful presence that the viewers can’t deny his importance in the show.

Lucifer redefined the “Devil” character in his own way, especially Mark Pelligrino’s portrayal of the Archangel, which captured the essence of Lucifer’s hate towards humanity superbly. Although he was the master of deception and the true depiction of evil, Lucifer stayed true to his intentions and character till the very end. He always gave the Winchesters a tough time, and the audience loved him for it.

Crowley is as Savage and Funny as he Can Get

  • Crowley first appears in Season 5, Episode 10.
  • His character was well-perceived as the King of Hell and one of the main antagonists of the series.
  • Crowley’s last appearance was in Season 12, Episode 23.

There was never a demon who gave the Winchesters as much of a tough time as Crowley. This snarky character did justice to his title of being the King of Hell and the Crossroads. He practically created backstabbing, and it never fails to amuse the fans. Every time Crowley assures someone that he’s on their side, he throws them under the bus the first chance he gets. It’s hard to say what category Crowley qualifies since he transitions between several things from a villain to an anti-hero, but that exact ambiguity is the most attractive thing about his character.

He always adds that much-needed sarcastic humor to dire situations and keeps the Winchesters on their toes. His wit, charm, and affinity for coming up with a classic twist in what seems like an impossible task are a few of the things that make his character worthwhile and a fan-favorite.

Charlie Bradbury is a Breath of Fresh Air

  • Charlie first appears in Season 7, Episode 10.
  • She’s an IT expert and an important person to the Winchesters.
  • She makes her final appearance in Season 14, Episode 6.

There aren’t many characters as truthful and pure as Charlie on Supernatural. She’s a rare gem and one of the few ones with no ulterior motives and a high resistance against betraying people. She’s introduced as a computer hacker in Season 7 and quickly becomes a go-to person for the Winchesters in times of trouble. With her sparkling and nerdy personality, Charlie manages to charm the viewers into loving her without a thought.

When she’s unexpectedly thrown into the “hunting” world, she admirably accepts her role and does everything to stay true to the purpose. Charlie’s death was one of the saddest in the series, and it completely shook the Winchester brothers. Her contagious smile and attitude balanced the occasional gloominess of the show. She was an adorable addition to the cast and deserved better treatment by the writers.

Jody Mills Was a Parental Figure For the Winchesters

  • Jody Mills first appears in Season 5, Episode 15.
  • She’s a motherly figure to Sam and Dean Winchester.
  • Jody’s last appearance on Supernatural is in Season 15, Episode 19.

Jody can be considered a male version of Bobby with a more badass personality and killer hunter moves. However, above all, she was an extremely caring and kind-hearted person, especially to the Winchester boys. She played a motherly role in their lives and kept them in check even when their real mother came back from the dead. Jody is the kind of strong female character who can carry a show on their own.

She went on to become a fan-favorite character after her debut in Season 5 and remained a strong support and ally of Sam and Dean. Besides being an incredible emotional support to the Winchesters, Jody also adopted protected girls who were lone hunters or had supernatural abilities. Jody Mills is hands down one of the best Supernatural characters, with absolutely nothing about her that the viewers would dislike.

Bobby Singer is the Winchesters’ Rock

  • Bobby first appears in the finale of Season 1 (Episode 22).
  • He’s one of the closest things to family to Sam and Dean Winchester.
  • His final appearance is in Season 15, Episode 20.

Bobby is the closest thing to a father for Sam and Dean. He was always protective of them from a very young age and indulged in keeping them “kids” rather than turning them into hunters. Bobby went on to become a series regular after Season 1 and was always a source to turn to whenever the Winchester boys were in trouble or couldn’t crack a case. Bobby’s popularity rose so much that the show brought him back multiple times from the dead because no other character could compare to his grumpy humor and sassy remarks.

His “Idjits” is perhaps one of the most popular words on the show after Dean’s “Pie” and “Sammy.” One of the best things that made Bobby a prominent character is his infinite knowledge of the supernatural and the hunting world. Sam and Dean would probably be possessed or rotting in hell without him.

Sam Winchester Was Destined For Great Things Since the Start

  • Sam Winchester first appears in the pilot episode of Supernatural .
  • He was destined to be Lucifer’s vessel even before he was born.
  • Sam’s final appearance on the show is in Season 15, Episode 20.

Introduced as the more rebellious member of the Winchester family, Sam initially wanted nothing to do with the hunter life. He even went to college and was about to start a new life when tragedy struck him the same way it did when he was just a baby. He was destined to become Lucifer’s vessel, but that predicament led him to suffer tremendously. Sam can be considered a more empathetic and softer version of Dean, who always tries to be practical and considerate of others’ feelings.

However, Sam Winchester made his fair share of poor decisions, which often landed him in hot water with his big brother. This never changed the fact that Sam loved Dean more than anything. It completely broke him when Dean died and was sent to Hell for the first time. It’s safe to say that despite enduring the impossible, Sam tried to stay true to what he believed in and keep his heart in the right place.

Castiel Immediately Won the Fans’ Hearts

  • Castiel first appeared in Season 4, Episode 1.
  • Castiel is one of the main characters in Supernatural and an integral part of the story.
  • The angel last appears in Season 15, Episode 18.

Everyone’s favorite Angel first appeared in Season 4 and has been a series regular ever since. The first time Angels were introduced in Supernatural via Misha Collins’ most prominent character, Castiel, the fans knew that he was going to be a huge part of the story. Castiel’s more innocent days as an Angel coming to terms with the ways of the Winchester brothers instantly made the viewers fall in love with him. Cas’ storyline has been nothing short of a roller coaster ride, as he’s been put through the wringer more than any other character.

There are several “versions” of Castiel in Supernatural, from being a loyal Angel and Seraph to turning into a villain at times. However, he played every iteration to perfection till the last scene. Although there are mixed opinions about the way the show handled Castiel’s character arc towards the later seasons, he’ll always be the good old Cas – the Winchesters’ best friend.

Dean Winchester is the Heart and Soul of Supernatural

  • Dean Winchester first appears in the pilot episode of Supernatural.
  • He started out as a hunter, but it was later revealed that he was destined as Michael’s vessel.
  • Dean’s final appearance is in Season 15, Episode 20.

One look at the broody Dean Winchester and the fans knew that they might never get over him. Dean’s character manifested itself as a pop culture icon, with several of his one-liners and whacky performances becoming Supernatural staples. Dean’s character arc isn’t an easy one since he goes through literal hell to come out on the other end. Most of Dean’s initial personality stems from his strong desire to protect his little brother Sam after their father’s demise.

There might be no one that Dean loved most in his life, and a great part of his life had always been to be his brother’s guardian. However, Dean is a lot of things, from being a reckless soul to a human being who values others’ lives over his. One of the few things besides Dean’s intense brotherly instincts that the fandom had always applauded his character for was being utterly charming, funny, and captivating.


By Ivaylo Angelov

Ivaylo Angelov born in Bulgaria, Varna graduated School Geo Milev is Tvserieswelove's Soaps Editor and oversees all of the section's news, features, spoilers and interviews.