As far as deaths go on Supernatural, they happen pretty much every episode. That is the whole point of the show, isn’t it? Sam and Dean hear about a death or something funky and then they hunt the killer. On a show that focuses on many supernatural deaths, you’d never expect to be effected so emotionally by them, and yet, they hit you right in the feels. How different would Sammy and Dean’s lives be if Mary had lived? We’re not sure we can even think about that right now. In order to be considered, the character needed to have a relationship (friend, family, significant other) with Sam or Dean. Also, as they’ve died 10 times over, we’ve only included Sam and Dean’s Top 2 deaths.
13. Mary Winchester – Death shown in “Pilot”
Oh Mary, we never even knew ya! The flashbacks over the years really showed us how her death affected Dean and how it altered Sam’s life, never having even known her. It proves that her death was more tragic than we could have imagined.
12. Jessica Moore – “Pilot” Season 1, episode 1
We don’t think Sam ever truly got over Jessica’s death. How could he? She was killed the exact same way his mother was. And he spent many years of his life blaming himself for her death. Out of the two deaths in this episode, we felt that this made fans more emotional based on Sam’s guilt over the situation.
11. Dean Winchester – “Do You Believe In Miracles” Season 9, episode 23
Dean has died many times, let’s not forget “Mystery Spot”and his many deaths in that single episode. But when he died in this episode, we didn’t know how Sam would be able to go on. What is Sam without his big brother Dean? We all know that “Deanmon” became a thing after this point, but that didn’t last long – thank God.
10. Sam Winchester – “Swan Song” Season 5, episode 22
Two seasons after Dean went to Hell, it was Sammy’s turn and it was truly tragic. What might be considered sadder is that that Adam is still in Hell, when Sam got out quickly (sans soul). After nearly beating Dean to death, when Sam came back to himself, and said “I’ve got him, Dean” the tears just started to flow.
9. Castiel – “Hello, Cruel World” Season 7, episode 2
Cas was in the wrong for most of season 6, but that doesn’t mean that when he walked into that lake to sacrifice himself, we didn’t feel all the things. Especially when his trench coat floated back up and Dean took it after it washed up ashore.
8. John Winchester – “In My Time of Dying” Season 2, episode 1
John Winchester might not have been the best father in the world of Supernatural but that doesn’t mean it was easy to watch him die. He completely redeemed himself when he traded his life for Dean’s, and because of that, we still cry when we watch the episode where he dies.
6 & 7. Ellen & Jo – “Abandon All Hope” Season 5, episode 10
Ellen and Jo’s deaths go hand-in-hand. We were so emotional when we realized that Jo was not going to survive her hell hound-inflicted injuries. But what really threw us over the edge was when Ellen decided to stay with her daughter. When the store exploded, we didn’t have words to express our emotions for that moment. We still haven’t fully forgiven Dean and Sam for not figuring out a way to save them.
5. Dean Winchester – “No Rest For The Wicked” Season 3, episode 16
This death was so sad, because we hadn’t experienced Hell in all it’s horrifying glory yet. We had no idea what was in store for Dean. Nor did we believe he’d ever be able to make it out. We really believed Dean would find a way to avoid this moment and were were absolutely crushed when he didn’t. That scene with the hell hounds was brutal.
4. Sam Winchester – “All Hell Breaks Loose, Part 1” Season 2, episode 21
Out of all the times Sam has died, this one gets us this most. When Dean tries to tell him it’s not that bad, we still break down in tears. If only we could have known when we first watched this episode how many times we would have to watch Sammy die.
3. Bobby – “Death’s Door” Season 7, episode 10
Watching Bobby die, after seeing him deal with all his inner demons in his mind, was one of the hardest moments Supernatural fans had to go through. Even before John Winchester died, Bobby had become a father figure to Dean and Sam. So that moment when he’s telling his father that he went on and “adopted two boys and they grew up great”, we just knew he wasn’t going to survive that gunshot wound.
2. Kevin Tran – “Holy Terror” Season 9, episode 9
Kevin’s death was heartbreaking for obvious reasons. What was saddest about his death was after the matter. As Dean cried by his body, we all thought about their earlier conversation where Kevin flat out tells Dean how he puts himself on the line for the Winchesters and bad things always happen. Well, as if that wasn’t bad enough, fans had to deal with the fact that he was murdered by an angel using Sam’s body. What made his death even sadder was when we found out a few episodes later Mrs. Tran was alive and asked to see her son after she was rescued.
1. Charlie – “Dark Dynasty” Season 10, episode 21
Fans were torn between our top 3, but most fans agreed with us that Charlie’s death was easily the saddest, because we don’t understand why it happened. Did Charlie really have to leave us so soon? We didn’t get to see her death on screen, and maybe that is for the best in this situation. At least Sam and Dean gave her a proper hunter’s burial, even if they couldn’t save her.
The general consensus from most fans was that the top 3 saddest deaths are also the top 3 characters that did not need to die. Supernatural, we’re still mad at you.
Honorable Mention: Baby – “Devil’s Trap” Season 1, episode 22
After the boys escape from Baby, she is totaled by a demon-possessed driver. Thankfully, Baby is restored quickly.