15 saddest Supernatural moments in the last 12 seasons

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We had 12 seasons of blood, sweat, and tears. Lots and lots of tears. Just what have been the saddest moments on ‘Supernatural’?

Supernatural is no stranger to saddest. The very first moment showed that there would be death and despair. Demons would take without remorse, and hunters would have no choice but to kill seemingly innocent people because of the monsters in the world. Throughout the last 12 seasons, we have cried like babies.

In fact, we’re not the only ones. The stars of the show have found themselves unable to stop the tears after shooting. There have been times reshoots have been needed because the emotions were too strong! Not many TV shows out there can claim to needing to do something like that.

More from Supernatural

Supernatural Season 13 is expected to be full of more sadness, betrayal, and despair. After all, it’s picking up where Season 12 left off; with Castiel dead and Mary stuck in the alternate world. SDCC 2017 made it clear that Dean and Sam are at opposite sides of how to handle their current situation.

There is just over two months for the new season of the show. Before we get into it, it’s time to look at the 15 saddest Supernatural moments in the last 12 seasons. Get your tissues ready, because you will need them!

#15 Season 8 “Goodbye Stranger”: Castiel beats Dean almost to death

When “Goodbye Stranger” opened, fans were shocked. Castiel broke Dean’s arm and then stabbed him without any remorse. Luckily, it soon became clear that this was just a simulation but an attempt for Naomi to turn Castiel against the Winchester brothers. Killing Dean was the ultimate test to show that Castiel had no underlying feelings for the brothers.

By the end of the episode, fans feared the worse. Castiel beat Dean to a pulp. At first Dean told him to do it, but then started telling him that he knew it wasn’t Castiel. All the while, Cas continues to punch Dean in the face.

Just as Cas is about to fire the final blow with the angel blade, Dean says something that broke fans hearts. He made it clear that Cas was part of the family and that he needed Cas in his life. The Destiel fans screamed, while others wiped away their streaming tears hoping that it would be enough to get through to Castiel and break Naomi’s mind control.

"“We’re family…I need you.”"

Fans breathed a sigh of relief when Castiel made the right choice and felt remorse for everything he had just done.

#14 Season 1 “Home”: Dean calls his dead

Episode 9 saw the Winchesters return to Lawrence, Kansas, thanks to one of Sammy’s visions. They needed to go back to the home they’d left behind, possibly facing the creature that had killed their other all those years ago.

There were certainly some heartfelt moments throughout the series, but none like the moment that Dean calls his dad, begging for his help. It was the first time in Supernatural that fans saw this 26-year-old hunter vulnerable. He still remembered his childhood in that home and remembered his mom. Going back home was a nightmare situation, especially if they were facing the thing that had killed her.

To make it worse, Dean had gone straight to John’s voicemail. He didn’t even get to talk to his dad, and instead had to leave the heartbreaking message on his answer machine in hope that John would receive it.

By this point in the series, fans wanted to see the Winchester brothers come face to face with their dad. They wanted to see the family reunited. If only the brothers had realized John was at Missouri’s house in the end.

#13 Season 2 “Everybody Loves a Clown”: Dean smashes up Baby

Nobody was allowed to touch Baby. Nobody at all. Yet, Dean did the one thing fans knew he would later regret. He took a crowbar to the car, taking his anger out on her because it was the closest thing to him and John Winchester.

To put the whole thing into context, this was just after John’s death. Dean didn’t know how John suddenly died and he’d come back to life, but he knew that something strange had gone on. And after just getting back in touch with his father and learning that Sammy could be dangerous, Dean was angry for his dad leaving him with the responsibility of keeping his little brother safe yet again.

Taking the anger out on Baby was poetic. The car was the closest thing to John, since it was Daddy Winchester’s first. It was a clear sign that Dean was angry at his father, and this was his chance to release that anger and be able to move on in some way.

Smashing Baby up made another thing very clear: the pain and sadness ran deep. The SPN Family gets chills every time that scene comes back on.

#12 Season 2 “What Is and What Should Never Be”: Dean at John’s grave

The first two seasons are full of sadness and tears. Season 2 gave us a hint of what could have been when Dean is pulled into a “wish world.” Really, it’s the Djinn playing on Dean’s subconscious, showing what life could have been like had Mary Winchester not died. By the way for The Walking Dead fans there is a humorous foreshadow of Jeffrey Dean Morgan with a bat hinting at the idea of Lucille.

During the dream world, Dean learns that the monsters and demons are still out there. The difference is that the Winchester brothers were never there to save people. Innocents died instead, and Dean soon realized that it was up to him and his brother to continue saving people.

On the night of realizing everyone has died, Dean goes to John’s grave with a selfish but understandable rant. He just wants to know why it’s up to the Winchesters to save everyone. Why wouldn’t they have their happy life? Why couldn’t Sam have Jessica alive? Sure, as brothers they were estranged, but Dean would live with that if Mary was alive and Sam was happy. So not entirely selfish.

In the end, Dean does decide to get himself out of the dream world. But the tears as Dean realizes he has to do that is heartbreaking.

#11 Season 8 “Sanctuary”: Sam admits his confession

By Season 8 of Supernatural, the Winchesters’ relationship had been up and down. One minute they would sacrifice everything for each other and the next they would barely trust one another. Throughout Season 8, they looked for a way to close the doorway to Hell for good, but it was in the season finale that Dean learned it would mean death for Sam.

While stopping Sam from closing that doorway to Hell, Sam shared his confession. It certainly wasn’t anything fans (or Dean) expected. Sam believed his sin was all the times he had let his brother down. It was a stark reminder that Sam looked up to his brother throughout his life, and the last eight seasons had worked their way to this point.

Of course, this also led to one of the saddest Supernatural moments for Dean. He realized just how much pressure he had put on Sam and how much they had recently questioned one another. He came out with one of the best lines of the season.

"“Don’t you ever think there is anything, past or present, that I wouldn’t put in front of you!”"

Unfortunately, the relationship wouldn’t remain sunshine and rainbows. Seasons 9 and 10 drove wedges into them, until they were almost at breaking point.

#10 Season 6 “Let It Bleed”: Ben and Lisa forget Dean

There are debates over whether Lisa was right for Dean or not. Some people liked her and Ben and others despised the whole storyline. Regardless of the side you’re on, the ending to the Dean-Lisa-Ben storyline is one of the most heartbreaking moments.

When Lisa’s life is in danger after being possessed by a demon, Castiel heals her of her injuries. However, Dean knows that Lisa and Ben will remain in danger forever while they know about the supernatural and the Winchesters. To keep them safe, he asks for Castiel to erase their memories.

While Sam is disappointed with Dean’s choice, it was clearly the best decision in that moment. It also wasn’t an easy decision. Dean was clearly heartbroken at the idea of losing a girlfriend and stepson, and he didn’t need his brother questioning his decisions. After all, it was his brother who had pulled him back into the hunting lifestyle after getting a year out.

#9 Season 2 “Heart”: Sam kills Madison

There are some transformations that people just can’t come back from. In Season 2’s case, it was the transformation into a werewolf. Sam’s latest love interest learned that she was the werewolf in San Francisco and that the attempt to return her to human didn’t work. She couldn’t control her change, so decided it would be best to die.

Unfortunately for Sam, she didn’t have the guts to kill herself. She selfishly asked Sam to kill her instead. Dean did offer, but Sam decided that this was something he needed to do.

Tears streamed down his face as he walked into the living room to kill his werewolf girlfriend. It was two for two when it came to women in his life dying due to supernatural reasons.

But it wasn’t just Sam’s grief. Dean’s single man tear told fans that he was upset about this too. It wasn’t the death of Madison, but his heartbreak that Sam had decided to do something that he would never be able to come back from.

#8 Season 2 “All Hell Breaks Loose Pt. 2”: Dean mourns over Sam’s body

Dean Winchester had spent the first two seasons looking after his little brother. He had done everything in his power to keep Sammy safe, including making an enemy of other hunters. It all came to a head in the Season 2 finale, when Sammy was stabbed and died in Dean’s arms.

Fans knew what Dean would choose to do in the end. Before Dean sold his soul, he watched over Sam’s dead body. Guilt took over, as he apologized for his inability to keep his brother safe after all. It was his screams, as he questioned what he was supposed to do now.

The SPN Family cried their eyes out throughout the scene. Despite knowing just what Dean would do next, they could feel the grief from Dean throughout the scene. The tears felt real and Supernatural fans around the world couldn’t help but wonder what their reactions would be like to a sibling dying in front of them.

"“You know when we were little, you couldn’t have been more than five, you started asking me questions…I remember I begged you to quit asking, Sammy, you don’t want to know. I just wanted you to be a kid, just a little while longer.”"

#7 Season 12 “Stuck in the Middle (with You)”: Castiel says goodbye

Season 12 has been a tough season for fans. It’s pulled the show back to some of the earlier settings and feelings, including some of the most heartbreaking moments. One of the saddest Supernatural moments from the season has to be when Castiel believed he was dying.

After Mary accepts a job from the British Men of Letters, the Winchesters and Castiel go up against another Yellow-Eyed Demon. They also get their hands on the Lance of Michael, which just so happens to kill good and bad beings (and the good ones slowly). When Castiel is hit with the staff, he goes through an excruciating death.

This slow death does give him a chance to say goodbye to his friends. He tells the Winchesters just how much he loves them all, and thanks them for allowing him to be a part of the family.

Fans feared the worse, unable to see a way out. They then cheered when Crowley did something for the greater good: broke the Lance of Michael and destroyed the magic that was slowly killing Cas.

#6 Season 4 “On the Head of a Pin”: Dean gives up the fight

Castiel has a special request for Dean. Knowing that he was a devilish torturer in Hell, Castiel asks Dean to torture Alistair. The elder Winchester brother agrees, but he clearly isn’t happy with doing it; despite it being on a demon who deserves it.

The torture sessions goes wrong, but not before Dean hears that he was the first seal. Had he not broken in Hell, Lilith wouldn’t have been able to break other seals to release Lucifer.

When he questions Castiel about the first seal, he learns that everything Alistair had said was true. Recovering from injuries and weakened, Dean breaks down. He doesn’t want the weight of the world on his shoulders anymore. Dean doesn’t believe he’s strong enough to take on Lilith, and he wants Castiel to find someone else.

This was the first time that Dean had ever broken so much that he had given up. Before this point he had considered giving up, but never fully gone through with it. Fans saw a fully vulnerable and damaged Dean.

#5 Season 12 “The Raid”: Dean kicks Mary out

There was a lot of hope for Season 12. Mary Winchester had been brought back from the dead, and this was a chance for the Winchester brothers to reconnect with their mother. Well, in Sam’s case, it was a chance to learn more about her.

Unfortunately for the Winchester brothers, Mary decided to leave them and find her place in the world alone. That led to her working with the British Men of Letters. Dean certainly wasn’t happy with that idea, especially after the way Sam had been tortured earlier in the season. He made his unhappiness extremely clear.

The SPN Family was left divided. While many wanted to be on Dean’s side, they could understand some of Mary’s thought process. She wanted out of hunting and never wanted the life for her sons, and would work with a group that seemed to want the same.

However, fans ended up on Dean’s side, has he shared just how hard it was for them. They had grieved for their mother and never expected her to return. Now she was back and wanted to work with an untrustworthy group instead of her own sons.

"“Our whole lives, you’ve been gone. You said that you needed time. No, you said you need space. So we gave you your space.”"

Dean let all his feelings out in the one scene. He made it clear just how much he resented his mother’s choice, and fans were heartbroken because of it.

#4 Season 4 “Heaven and Hell”: Dean tells Sam the truth about Hell

If giving up wasn’t enough for Season 4, the saddest Supernatural moment of the season was Dean sharing the truth about Hell with Sam. He told his younger brother everything about torturing innocents, and did it without making eye contact once.

For the first 10 episodes of the season, the SPN Family had seen Dean going through PTSD. He drank more, couldn’t sleep well, and continuously thought about the souls he had tortured. It was the life of a soldier, who had done things he regretted or didn’t necessarily agree with.

What made this scene heartbreaking were Dean’s tears. There were completely real. In fact, this was one of the scenes that Jensen Ackles had to walk away from after filming, because he just couldn’t stop crying. He also had to film it again because the emotions were just too much. Could you imagine how heartbreaking the first version would have been?

#3 Season 12 “Who We Are”: Dean tells his mom he hates her

After the scene in the raid, Mary and her sons attempted to patch things up. Unfortunately, the British Men of Letters got in the way. They used mind control over Mary and made her into a ruthless killer, who even wanted her sons dead. Dean decided to go into his mother’s head to try to bring his mom back.

While in her head, he realized that she was choosing to remain in the dream world that was created for her. She chose to remain with her sons in a setting from 30+ years ago. Dean was understandably angry.

It came to the moment that had been building for the whole 12^th season. Dean made it clear just how he felt about his mother. How he hated her, but how he loved her at the same time. Fans could see the resentment, anger, and pain in Dean, as Mary just tried to ignore everything that was being said. The SPN Family turned against Mary completely in those moments for making Dean feel the way he did.

There have been very few times that Dean has told someone he hates them but loves them. Only family can make you feel that way.

#2 Season 7 “Death’s Door”: Bobby’s death

There have been many deaths over the years. They’ve been sad, but nothing has been as sad as this one. Bobby was a surrogate father to the Winchester brothers. They didn’t just see him as a dad, but he viewed them as sons. This was more than just a hunter dying, for the Winchesters and the fans.

Supernatural’s seventh season isn’t a favorite for many fans, but all tuned in to find out if Bobby was going to make it through the bullet to the brain. In the end, he woke up long enough to give Dean vital information but then passed away. Dean and Sam could just watch as doctors moved around them and tried to save their father figure.

It was the scene after this that broke the fans, though. Bobby went back into his last memory, where it was Sam, Dean, and himself relaxing after a hunt. Rather than fighting monsters together, his most special moment was a time when they were just a family enjoying food and TV.

This wouldn’t be the last time Bobby would be seen. Season 8 focused on him as a spirit and he has been back once a season since then. Now fans hope that Jim Beaver will return for Supernatural Season 13.

#1 Season 12 “Regarding Dean”: Dean tries to remember who he is

When attacked by witches, Dean forgets who he is. His memories slowly disappear, and we get a magical insight into dementia. After being told something, Dean almost instantly forgets.

At first, there is some humor in the episode. While Rowena explains to Sam about how Dean will slowly die, Dean comments how it “sucks for that guy.” He has no idea that Rowena is talking about him because of this memory loss.

There’s one scene in particular that stands out and is takes the top spot in the saddest Supernatural moments. We don’t just see dementia from the view of people Dean loves, but from Dean’s perspective. He looks in the mirror and attempts to hold onto the memories. He reminds himself of his name, his family, and even his best friend. Yet, within the few minutes of initially remembering, he slowly starts to forget. There’s fear, pain, and sadness in his eyes that makes it clear just how heartbreaking dementia is for everyone.

Next: 'Supernatural' Season 13: 3 ways Castiel could return

Do you agree with this list? What are your saddest Supernatural moments throughout the 12 seasons? Feel free to share them in the comments below.

Supernatural returns with its 13^th season on Thursday, Oct. 12 at 8 p.m. on The CW.

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15 saddest ‘Supernatural’ moments in the last 12 seasons

By Alexandria Ingham | Jul 29, 2017