While Supernatural may be a show that explores horror and fiction, it still manages to pack an emotional punch with many of the deaths depicted in the show. Supernatural is easily the most successful and beloved show to come out of The CW. The series ran from 2005 until 2020, with a total of 15 seasons, and this longevity was largely down to the dynamic relationship between the two stars, Jared Padalecki and Jensen Ackles, who play Sam and Dean Winchester respectively.

The Winchesters are part of a small and secretive trade which extends back into ancient times, known as hunters. They put their lives on the line to keep the world safe from dangerous beings who are the literal stuff of nightmares. From demons, to monsters, and occasionally even militant angels, the Winchesters risk everything to save the world in secret. However, putting themselves and others in harms’ way has resulted in more than their fair share of casualties along the way.

12

Madison

Madison appears in just one episode of Supernatural during season 2, where she and Sam form an instant connection. Madison was the first person that Sam opened his heart to after Jessica’s brutal death at the beginning of the series, and as such, this was something incredibly special and unique for him. Sam and Dean meet Madison while on the hunt for a werewolf who has recently murdered a string of people. However, they soon discover that the werewolf is actually Madison, who was recently turned and unaware of her condition.

The boys try to desperately find another way, hunting down and killing the werewolf that turned her in the hopes of curing her, which they initially believe works. When Sam believes Madison is cured, they drop their guards and sleep together, but then Madison turns after this moment, proving the cure didn’t work. Despite Madison’s brief appearance, her death, begging for Sam to kill her and prevent her hurting anyone else, is one of the most moving and devastating on the show.

11

Jessica Moore

Almost exactly 15 months earlier, Sam lost another great love of his life to the same monster that killed his mother when he was an infant. Jessica Moore was Sam’s girlfriend, whom he met while studying in college. Sam had chosen to leave the family business behind and create a life for himself. However, when Dean reentered his life, he learned quickly that he could never truly leave that life behind.

Sam had gotten extremely close to Jessica, and was beginning to plan a life together with her and a potential future. Despite his plans, and his efforts to leave hunting behind, Jessica became one of the first victims Sam couldn’t save when he was pulled back into that life due to his father’s disappearance. Jessica also appears in a single episode before being killed, but considering it’s the pilot, and it establishes a strong motive for Sam to return to hunting, it hits extremely hard.

10

Ellen & Jo Harvelle

Jo Harvelle was a young woman who grew up without her father, due to him dying while he was on a job as a hunter. While this tragedy made her mother Ellen extremely wary of hunters and the whole profession, Jo became obsessed with following in her father’s footsteps. However, it wasn’t until she met Sam and Dean that she had her first opportunity to go on a hunt and officially start her career as a hunter. In order to protect her daughter, Ellen chose to join her in becoming a hunter, and together they became a formidable duo that operated for years.

However, the life expectancy for most hunters is nearly always brief. When Ellen and Jo join up with Sam and Dean a few years after they initially met, Jo meets her end protecting the boys, and being mortally wounded by hellhounds. Ellen, refusing to live without her daughter, chooses to stay behind and hold back the other monstrous demons to let Sam and Dean escape, while holding her dying daughter in her arms in a beautiful and heartbreaking sacrifice.

9

Kevin Tran

Kevin Tran is one of the characters that only joined the show after the halfway mark, when the storylines began to move more into the spiritual with the introduction of angels, prophets, and Supernatural’s God himself, Chuck. Kevin was a young teenager selected by Chuck to become a prophet, but the burden weighed heavy on his youthful shoulders. Quickly, Kevin learned that being a prophet put himself and everyone he loved in danger, and it led to a sheltered and restrained life.

Sam and Dean genuinely cared for the boy, and chose to try and help and support him and his family however they could. Eventually, this bond became familial, after the boys had worked with and protected Kevin for years. However, when an ambitious angel named Metatron attempts to perform a hostile takeover of heaven, Kevin becomes a pawn in his war. Metatron ordered Gadreel, an angel who was possessing Sam’s body, to murder Kevin, which he did. This devastated Dean, who lost his brother to the angel, and Kevin by his hand.

8

Crowley

Crowley may be a demon, but he is shown to have a heart through his numerous appearances on the show and his arc from crossroads demon, to the King of Hell, who makes every effort to help the Winchester’s even to the extent of sacrificing himself. Crowley appears more than any other demon in the series, with his interactions with the boys revealing a slow, but steady change of heart over time.

In season 12, Crowley is instrumental in preventing a Lucifer from an alternate reality from breaking through and into the one where the Winchester boys exist by laying down his own life. After working so hard for so long to get everything he ever wanted, Crowley shows his true colors by putting the boys and his own reality first, and paying the ultimate price.

7

Charlie Bradbury

Charlie Bradbury quickly became a fan favorite character after her first appearance in Supernatural season 7. She had abundant confidence, and wasn’t afraid to talk back to the boys, despite the clear disparity between their heights and physical builds. Charlie knew where her skills lay, and she felt comfortable being her genuine authentic self.

Charlie became a recurring character who worked with the boys for multiple adventures. However, Charlie still wasn’t a skilled fighter, and when the monstrous Eldon Frankenstein came looking for answers, Charlie stood in the way. As a result, Eldon stabbed Charlie to death numerous times, resulting in a brutal and traumatic death for one of the most beloved recurring characters on the show.

6

Rowena MacLeod

Just like her son Crowley, Rowena MacLeod had an incredible arc through the Supernatural series. She joined the show much later in season 10, but from the first moment she appeared, she made an impression on the boys and the audience. Rowena was a powerful witch who had survived for centuries before meeting the boys. And while she was not a great mother to Crowley during his life, she found ways to honor and bond with her son when he was a demon.

Rowena joined the Winchesters and their other friends ahead of the final conflict of the series in season 15. As her son sacrificed himself to protect the Winchester’s and preserve their reality, Rowena sacrificed herself to save the world. Rowena selflessly gave up her body and her life, despite centuries of doing anything to preserve it, in order to help the Winchester’s send all of the demons and lost souls back to hell.

5

Castiel

Castiel became a staple in the Winchester team after Supernatural season 4. Once again, he had an incredible arc that saw him transform from a cold, emotionless angel, into a compassionate, loving friend to the boys, with a special affection for Dean Winchester. Castiel grew enormously in numerous ways, but it came gradually.

In the final season of Supernatural, Cas suffers a fate worse than death as he sacrifices himself to save Dean by expressing his true feelings and obtaining a sincere moment of happiness. Cas had made a deal with the Shadow, promising to be absorbed into the Empty in a moment of pure happiness in exhange for Jack’s life. He then uses this promise to his advantage in order to summon the Shadow and have it take him and Billie to the Empty, thus protecting Dean.

4

Bobby Singer

Bobby had been an instrumental part of the team from the very beginning, and in the absence of the boys’ father, Bobby became the remaining father figure in their lives. Despite often having harsh words to describe the boys, he had genuine love for them and did all he could to protect and support them in their role as hunters, and simply as good men.

However, despite Bobby usually avoiding the action himself, in season 7, he becomes the unfortunate victim of the undercover leader of the leviathans, Dick Roman. After years of helping the boys, Bobby meets his end when a stray bullet hits him directly in the head, which lands him in critical condition before his resulting death. The love between him and the boys makes this death deeply emotional, and one of the most upsetting of the entire show.

3

Sam Winchester – The First One

Death works differently in Supernatural, and many of the characters in the show tend to find some way to work around death. Whether that be a deal with a crossroad demon, the touch of an angel, or literally pulling them out of purgatory, the Winchesters and their friends can often find ways to keep getting back up when they are knocked down. However, in the early seasons, when the boys meet their first taste of death, this tradition of resurrection has yet to be established.

This means, that when Sam dies for the first time in Supernatural, it feels incredibly haunting and final. Dean had already lost every other member of his family, and Sam had tried to escape from life as a hunter. But despite all of this, Sam meets his end by being stabbed in the back just as he thinks he is clear of danger. At the end of season 2, when Sam is dragged into a battle royale fight to the death with other special children who have been given demon blood, Sam is stabbed in the back with his own knife in one of the most devastating season finales of all time.

2

Dean Winchester – Death By Hellhounds

While this incredibly emotional loss is short-lived thanks to Dean making a deal with a crossroads demon, this event does lead to the next most emotional death of the series. Dean had already tasted death earlier in the show, but none were quite as brutal as when he was killed by hellhounds that savagely tore him apart. This moment was a direct result of his earlier deal to save Sam.

Dean had promised his soul to a crossroads demon in exchange for Sam’s life. He hoped to use the 12 months he was given ahead of the deal being collected so that he could find a way to outrun his death, but nothing worked. Dean was followed by hellhounds ahead of his death, building tension and anxiety on his part ahead of his awful demise.

1

Dean Winchester – The Last One

However, the saddest and most painful death to take place in Supernatural is in the very last episode, when Dean dies for the final time. After spending years fighting side by side with his brother, the pair finally put the world to rights. No more trouble from the powers above as God left the universe, no more struggles with Lucifer, the threat of a Nephilim, or the gates of hell opening up.

All that was left were a few monster nests for low level creatures. This was the easiest and most relaxed the boys could be in their entire lives. However, just when it seemed like they could drop their guard a little, Dean was pushed into a wall where a stray bar was extending out. Dean was fatally wounded, and despite the journey that came before, he made Sam promise not to bring him back, but instead go and live his life. The final goodbye in Supernatural, and the end of the Winchester’s story together.