Twelve of Supernatural’s Most Heart-Wrenching Moments

Since 2005, Supernatural has been great at breaking hearts. The show is well-known for their highly emotional scenes, which often leave viewers with at least a couple of tears in their eyes.

With the frequency of these scenes, it would be nearly impossible to name every sad moment on the show. So, instead, in honor of the series’ upcoming twelfth season premiere, we’re giving you twelve of Supernatural’s most heart-wrenching scenes.

Warning: If you are not caught up, there are spoilers ahead.

1. The moment Dean threw away the Samulet (5×16)


Back when the Winchester brothers were just kids, Sam obtained an amulet from Bobby for his dad. When he didn’t show up for Christmas, Sam decided to give the gift to his older sibling instead. Dean kept and wore it for years but near the end of season five, things changed and he threw it out. Not only did it practically symbolize the older Winchester tossing out their brotherhood, but Dean decided to do it right in front of Sam. Rough times.


2. The moment Castiel admitted to working with Crowley (6×20)

After believing in the angel for so long, Dean, Sam, and Bobby’s trust in him was destroyed during season six. When the three of them trapped him inside a circle of fire, they demanded the truth. Dean asked Cas to look him in the eyes and say he wasn’t working for Crowley, but he was unable to do it. He then admitted to working with the demon behind the Winchesters’ backs, although he claimed it was to protect them. It, for obvious reasons, put them on shaky ground.

3. The moment Dean and Sam had to kill Madison (2×17)

Not too long after Sam lost Jessica, the young hunter met Madison. They seemed to connect instantly. This shouldn’t have been a problem, but the woman was bitten by a werewolf. On certain nights, Madison would turn and go out, killing people without any knowledge of it when she woke up. In order to stop her, there was only one thing the Winchesters could do: kill her. After a small debate, Sam is the one who picks up the gun.

4. The moment Dean Winchester said his goodbyes (11×23)


To kill Amara, Rowena put a bomb inside Dean so when he stepped near her, he’d explode and take her out. Unfortunately, the method would kill the eldest Winchester brother as well. He got the time to give his goodbyes to both Cas and Sam, and each one is heartbreaking in its own way.


5. The moment Sam got drunk (2×11)

While the boys regularly pick up a beer, seeing them drunk is an uncommon sight. When Dean comes back to his and Sam’s motel room one night, he finds his little brother completely wasted. It’s funny until it’s not.


6. The moment Mary sacrificed herself to save Sam and Dean (1×09)


When Sam and Dean returned to their childhood home for a case in season one, something very unexpected happened: Mary Winchester showed up. While she was only around for a couple of moments, it was the first time Dean has seen their mom since he was a kid. And because Sam was so young when she was killed, it was really his first time ever seeing her outside a photograph. In order to save them, she sacrificed herself.


7. The moment Sam and Dean found Charlie (10×21)


To rid Dean of the Mark of Cain, Sam was trying everything he could think of. He eventually brought others into the fight, including Charlie, which sadly led to her death. The Winchesters got a call from her but by the time they got there, it was too late.


8. The moment Rowena revealed why she hates Crowley (11×10)


Even the most powerful and evil characters have their moments. In the season eleven mid-finale, Crowley asked his mother why she hates him. Rowena gave a response that gave everyone a rare glimpse of her greatest vulnerability: love.


9. The moment Sam nearly died to finish the trials (8×23)


To close the Gates of Hell, there are a series of trials a person must go through. Dean Winchester was originally planning on doing them, but due to some complications, Sam ended up taking them on. During the final stage, it’s learned that the trials will kill him. While Dean sees it as a problem, Sam doesn’t, and it takes him a whole lot of convincing before he steps down.


10. The moment Lucifer that he, not, God, was sending Sam visions (11×09)


Throughout the beginning of season eleven, Sam was having visions. While Dean was a bit skeptical, he believed they were coming from God. In the end, it turned out that the younger Winchester was entirely wrong. Instead of getting messages from God, he was actually getting messages from Lucifer the entire time.


11. The moment Dean spoke about Hell (4×10)

For a decent amount of time, Dean stayed pretty silent about his experiences in Hell. Around the middle of season four, he finally confessed to Sam about what went happened down under. Not only did it sound miserable but Dean actually cried, and the Winchesters usually try to stay away from showing their emotions.


12. Every single moment Sam and Dean has died (2×22, too many more to count)

Over the course of eleven seasons, Sam and Dean have both died numerous times. Their deaths are never easy to watch. Usually, the other brother is right near the one dying, and there is always an emotional scene before it’s lights out.


Yeah, Supernatural is painful.

What scene got to you? Is there a moment we missed? Tell us by tweeting us over on our Twitter page, @CelebMix.

Written by Jessica Brown

A college graduate who enjoys watching Supernatural, attending conventions and concerts, taking photos, and writing to the masses. Email me at jesslaurenb@yahoo.com.