Supernatural: Top 10 Most Heartbreaking Deaths

Supernatural: Top 10 Most Heartbreaking Deaths

Supernatural has always had a habit of given characters the axe. Sometimes they come back, sometimes they don’t, but regardless it’s often a kick to the feels. This year’s two part season finale was no exception.  So in honor the grand tradition of Supernatural and Death I thought about presenting my top five emotionally draining Supernatural character deaths….but there are A LOT so I’m bumping up to Ten. Spoilers ahead obviously…


Last Warning!




Eileen Leahy


Played by: Shoshannah Stern

First appearance: S:11 E:11 Into the Mystic

How she goes out: Death by Hell Hound at the hands of the British Men of Letters

Eileen was a pretty kickass character in her own right. She became a Hunter to avenge the death of her parents at the hands of an Banshee, the incident also caused her to go deaf.

Okay, I’ll be the first to admit one of the reasons I loved Eileen so much, was that it meant that Dean Winchester repeatedly got to say my name, that little bit of narcissism aside, it was really great to have another female hunter around, and one who was a peer to the boys, as apposed to maternal (Mary, Jody), or bratty teen (Claire).


Mick Davies


Played by: Adam Fergus

First appearance: S:12 E:12 Mama Mia

How he goes out: Shot in the head by British Men of Letters Agent Arthur Ketch

Full disclosure I am a sucker for British accent, and Adam Fergus is pretty easy on the eyes.

After Mick was unceremoniously killed, I found myself more upset than I thought I would be, to be fair I wasn’t expecting him to go out so quickly either. Mick was yet another person to fall victim to the curse that is believing in the Winchesters. The boys had “turned” him, helped him see that not everything is black and white, that the world is full of grey areas. How as Hunters their job was not only exterminating the monsters, but saving people as well. Sam and Dean showed Mick that he had options.  Just as I was beginning to think he would make an (adorable) and helpful (think of all the MOL knowledge he possessed) assent to the Winchester “family” and he was ripped away from us.




Played by: Chad Lindberg

First appearance: S:2 E:2 Everybody Loves a Clown

How he goes out: Burned to death in the fire that burnt down The RoadHouse

Ash was definately a fun character. Whip smart and quirky with a mullet it was hard not to love him. Plus I always felt sad that he didn’t get a “real” death.



Rowena MacLeod


Played by: Ruth Connell

First appearance: S:10 E:3 Soul Surviver

How she (finally) goes out: : Burned to a crip by Luicifer

It is a sad but true fact that females on Supernatural don’t tend to have a very long life expectancy. The character of Rowena was truely a gift. She was cunning, sassy and powerful. Rowena was generally looking out for number one, which means that she could switch alegences at any given moment, which always kept you on your toes. And the fact that she was Crowley’s mother was an added delight.

AND She was another character burned to a crisp off screen…




Played by:

First appearance: S:2 E:15 Tall Tales

How he (finally) goes out: Stabbed by Lucifer, using his own Angel Blade

Lucifer has a tendency to off a lot of great characters, Gabriel was no exception. He was yet another victim of choosing the Winchesters side in the battle between heaven and hell. For the most part he kept to the sidelines, creating mischife and mayhem, but not really interfering, that is until he took his final stand.


Henry Winchester


Played by: Gil McKinney

First appearance: S:8 E:12 As Time Goes By

How he goes out: Stabbed By Abaddon

I will fully admit that part of my love for Granddaddy Winchester steams from my immense love of Gil McKinney himself. BUT that aside, Henry Winchester is yet another “ordinary” human who sacrificed himself in order to do what was right, and protect Sam & Dean. It broke my heart to see the boys loose yet another family member in the war between good and evil.


Ellen and Jo Harvelle


Played by: Samantha Ferris, &  Alona Tal (Respectively)

First appearance: S:2 E:2 Everybody Loves a Clown

How they go out: Explosion/Mauled by Hell Hound

So technically, this is two deaths but considering how they went out, I feel I get to call it one. Ellen and Jo were early editions to the Winchester’s surrogate family. I’m a sucker for strong female characters and Ellen and Jo were warriors in their own right. That’e what made their deaths so heartbreaking, they sacrificed themselves for the greater good.




Played by: Julian Richings

First appearance: S:5 E:21 Two Minutes to Midnight

How he goes out: Killed with his own scythe by Dean

I FRAKEN LOVED DEATH! Now there’s a statement you don’t see often. Seriously though, I do believe that Supernatural’s interpretation of Death is one of the best I’ve ever seen. From the absolutely BRILLIANT scene used as his introduction, to his love of food, and his willingness to “help” our boys, this was clearly not a version of Death like we had seen before. Which is what made his sudden “death” so dramatic. I am still holding out hope for him to come back.

It also leads to my questioning how people are still able to die if there is no Death, but that’s a WHOLE other issue.




Played by: Mark Sheppard

First appearance: S:5 E:10 Abandon All Hope

How he (finally) goes out: Suicide by Angel Blade

Remember what I said about Rowena generally looking out for number one? Well, like mother like son. Crowley was, of course, a demon, but that didn’t necessarily make him evil. He was an opportunist, striving to do whatever would benefit him most, be it teaming up with Lilith or the Winchesters. Despite not being billed as a series regular to Season 10, Crowley has been an integral friend AND foe to our boys for eight years. We’ve gotten to see his struggles with self doubt, power, even his own family, it would be impossible for him not to worm his way into our hearts. Despite all his struggles, Crowley has always been a survivor, and I think that’s what made his suicide (even if it was for the greater good) so upseting. It was sudden, heroic and heartbreaking.


Bobby Singer


Played by: Jim Beaver

First appearance: S:1 E: 22 Devils Trap

How he (finally) goes out: : His ghost is burned by Sam and Dean

A wise man [wink, wink] once said “Family don’t end in blood.” John Winchesters was many things, but a good father figure wasn’t one of them. Enter Bobby Singer, the Winchester brothers true dad. Originally conceived as a one off character, Bobby easily became a fan favorite and ended up sticking around for several seasons.

Not gonna lie every time Bobby died, yes that sentence is correct, I cried, like big fat sloppy tears. Hell, every time his character comes back, I cry like a baby.


So what do you think? Do you agree? Disagree? Which deaths hit you the hardest? Hit up the comments and let us know.



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