Supernatural's 10 most devastating character deaths (ahead of the finale)

Supernatural’s pilot quickly established a shocking and steadfast rule: Absolutely nobody is safe from the Grim Reaper. A sinister figure slaughtered Mary Winchester before the opening credits, and by the end of the episode, another individual near and dear to Sam met a similar grisly fate. Viewers came to expect Sam and Dean Winchester doing what they do best and slaying their ghoulish adversaries in gruesome fashion. However, even the Winchester siblings — and many of their closest friends, family, and allies — have ended up six feet under during the show’s 15 seasons.

Dean first earned a ticket to Hell when hellhounds tore him apart after his crossroads deal expired. That led to an extensive period of torment and suffering. Sam has also perished, most notably when the half-demon Jake knifed him in the spine. Dean consequently made a deal with another demon to resurrect him. The two have been killed on numerous other occasions… from being shot, mauled, stabbed, throat ripped out... only to somehow miraculously cheat Death in the end. And let’s not even mention the Trickster’s time loop where Dean was killed over and over again in increasingly innovative and cruel ways. 

Arguably the most devastating and heartbreaking goodbye transpired last week. The angel Castiel entered the picture back in Season 4. A fish out of water on Earth, he quickly became a fan favorite and extended member of the Winchester family as he discovered his humanity. However, after a touching declaration in the recent episode "Despair," Castiel allowed the Empty to claim him and their adversary, Billie, forever. Needless to say, Sam, Dean, and the rest of the Supernatural universe will never be the same again.  

In honor of the Nov. 19 series finale coming up on The CW, SYFY WIRE is looking back at the Supernatural deaths (outside of the core characters) that most rocked its fandom.  

Credit: The CW

First Appearance: “Pilot”

Death: “Pilot”

Targeted by Azazel, retired hunter Mary had the distinction of being the first character to meet her maker. The Yellow-Eyed Demon pinned Mary to the ceiling of baby Sam’s room, slit her stomach, and eventually set her ablaze. Mary’s gruesome demise forever scarred the Winchesters. It ignited her husband John Winchester’s thirst for vengeance and to raise his sons as hunters. 

Credit: The CW

First Appearance: "Pilot"

Death: “Pilot”

Jessica represented a normal life for Sam. Both were enrolled in college and in love. Best of all, Sam was free from the family business. No demons. No hunting. Period. That all came crashing down after Sam and Dean returned home from a caper to find Jessica plastered on the ceiling and bursting into flames… in the same manner their mother was murdered years ago. This pushed a heartbroken and angry Sam back into hunting. 

Credit: The CW

First Appearances: Season 2’s “Everybody Loves a Clown” 

Deaths: Season 5’s “Abandon All Hope”

A mother/daughter hunting team, Ellen never wanted her daughter to follow in her hunting footsteps. However, after her father died on a mission, Jo took up the good fight to honor his memory. Sam and Dean first ran into the Harvelles at their base of operations, the Roadhouse. The quartet didn’t hit it off immediately, but quickly became friends and allies. Jo even developed a crush on Dean.

Ellen and Jo participated in numerous missions and frequently provided intel for the Winchesters. After the demon Meg sicked a pack of hellhounds on Sam and Dean, Ellen and a mortally wounded Jo acted as bait. They detonated bombs that blew themselves and the hellhounds to smithereens. A grieving Dean vowed retribution for their deaths.   

Credit: The CW

First Appearance: Season 3’s “Time Is on My Side”

Death: Season 6’s “… And Then There Were None”

A semi-retired hunter with strong ties to Bobby Singer, Rufus first popped up when Dean required information regarding the location of Bela Talbot. He subsequently pitched in against Lilith and the Horseman War. Rufus ultimately met his demise when Bobby, under the influence of a Khan worm, mortally wounded him with a blade. Another colleague down for the count. 

First Appearance: Season 1’s “Devil Trap”

Death: Season 7’s “Death’s Door”

Almost nobody on this list meant more to Sam and Dean than Bobby. A rough, gruff, and loyal hunter, Bobby represented a father figure to the boys. He regularly participated in missions and doled out advice, until Leviathan Richard Roman shot him in the head. The beloved character slipped into a coma and tearfully passed away. 

Bobby may be gone, but not forgotten. He subsequently manifested as a ghost, in flashbacks, memories, and even an alternate Bobby from another dimension. 

First Appearance: “Pilot”

Death: Season 2’s “In My Time of Dying”

The father of Sam and Dean Winchester, hunter John went missing while pursuing the Colt, a mystical revolver capable of dispatching any hellish being, including the reigning Prince of Hell, Azazel. It wasn’t until the episode "Shadow" that the three finally reunited to stop Meg. After a demon-possessed demon crashes into the Impala, a gravely injured Dean lies at death’s door. To save his son, John makes a Faustian deal with Azazel: his life for Dean’s.    

Credit: The CW

First Appearance: Season 7’s “Reading Is Fundamental”

Death: Season 9’s "Holy Terror”

A regular high school student, Kevin originally crossed paths with Sam and Dean after the Leviathan Dick Roman unearthed the Leviathan Tablet. Kevin was named a prophet, and his life was never the same. Kevin proved instrumental in the fight against big bads Dick Roman and Metatron. However, the likable teen was shockingly disposed of by Sam, who was possessed by the angel Gadreel. Dean broke down in tears. Another fallen friend. 

Credit: The CW

First Appearance: Season 5’s “Abandon All Hope”

Death: Season 12’s “All Along the Watchtower”

A powerful demon who seized control over Hell in Lucifer’s absence, Crowley enjoyed a love/hate relationship with Sam and Dean. Half the time he promised to destroy them. The other half Crowley allied himself with the boys to thwart Lucifer, Leviathans, Abaddon, and other fiendish heavy hitters. Indeed, in order to close a rift and trap Lucifer inside, a life must be forfeited. Crowley takes the noble route and stabs himself with an angel blade, proving that perhaps he wasn’t all evil.    

First Appearance: Season 7’s “The Girl with the Dungeons and Dragons Tattoo”

Death: Season 10’s “Dark Dynasty” 

A hacker-turned-hunter, Charlie first encountered Sam and Dean while employed by the Leviathan Dick Roman. A self-professed nerd and fangirl, she defeated the Wicked Witch of the West before turning her computer skills towards freeing Dean from the Mark of Cain. Unfortunately, those efforts cost Charlie her life when Eldon Frankenstein stabbed her multiple times. Charlie viewed Sam and Dean as brothers, and Dean once called her “the little sister I never wanted.” This death really hurt. 

First appearance: Season 10’s “Soul Survivor”

Death: Season 15’s “The Rupture”

Formidable spellcaster. Mother of Crowley. Frenemy. Rowena’s lust for power often pitted her against the Winchester boys. After assisting Lucifer in escaping the Cage, he rewarded Rowena’s loyalty by snapping her neck. However, the resourceful witch resurrected herself with a spell she prepared in advance. Lucifer killed her a second time, but mortality didn’t suit her.

In the escalating battle against God, Rowena sacrificed herself in order to send all the demons and tortured souls running amok back to Hell. Sam took the loss particularly hard since the two had developed a certain fondness for each other.