The 10 Most Heartbreaking Supernatural Episodes

The 10 Most Heartbreaking Supernatural Episodes

Supernatural is coming to an end with its next season and there should be plenty of moments that touch the hearts of fans as they say goodbye to Sam and Dean and their cast of supporting characters. Of course, tears are not something that is rare on the show, as there have been plenty of losses and heartbreaks through the first 14 seasons of the show.

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Fans have seen beloved characters die, some which passed on forever. There have been moments where characters had to say goodbye and times where the ultimate sacrifice was made with shattered survivors trying to pick up the pieces. For a TV series with vampires and ghouls, there are a lot of touching moments in the Winchester household. Here are 10 of the most heartbreaking Supernatural episodes.

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The 10 Most Heartbreaking Supernatural Episodes
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10 In My Time of Dying (02.01)

The 10 Most Heartbreaking Supernatural Episodes

Supernatural season 1 did not go easy on Sam and Dean Winchester. The first episode alone saw the death of their mother, although Sam was a baby and Dean was very young. It also saw the death of Sam's girlfriend that set the brothers out on the road to find and eliminate the evil that infected their lives. Things got worse for the boys.

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By the end of season 1, it looked like Dean was on death's bed and it looked like he might die. No one expected this to happen since Dean was one of the stars but few expected that it would be their dad, John Winchester who sacrificed his own life to save that of his son. Seeing the boys lose their only remaining parent was a heartbreaking way to start the second season.

9 All Hell Breaks Loose (02.21)

The 10 Most Heartbreaking Supernatural Episodes

Not only did season 1 start out with a heartbreaking tragedy and ended with one just as shocking. In "All Hell Breaks Loose," Supernatural let the entire special children storyline with Sam play out and in this episode, all the kids were brought together to fight to determine who was left standing to become the Chosen One.

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Remember at the end of season 1 when it looked like Dean was going to die? Season 2 brought death to Sam. Dean arrives in the town to help Sam but he is too late and Sam is stabbed in the back and dies in Dean's arms. The elder Winchester brother had now lost his mom, dad, and little brother, and the tears were real in this one.

8 Dark Side of the Moon (05.16)

The 10 Most Heartbreaking Supernatural Episodes

By season 3, Sam and Dean seemed to both be on death's bed and came back, so seeing them die wasn't quite as shocking and heartbreaking as the first times. This is good because in one episode in season 3, Dean died 103 times. Anyway, head to season 5 to see not one, but two heartbreaking Supernatural episodes.

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The first came with "Dark Side of the Moon." In this episode, the show ups the ante a bit when Sam and Dean both die. With both dead, the brothers can't really do anything to bring the other back. However, what makes this episode so sad is that they go to Heaven and relive their past memories -- good and bad.

7 Swan Song (05.22)

The 10 Most Heartbreaking Supernatural Episodes

Season 5 ends with the big bang -- the Apocalypse. The boys have been trying to find a way to stop the Apocalypse to no avail -- even both dying and going to Heaven at one point and still coming back empty-handed. Now, with no other options, Sam Winchester finally gives in and agrees to become Lucifer's vessel in an attempt to trick him and send him back to his cage.

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After a battle, the boys win and stop the Apocalypse, but at the cost of Sam ending up trapped in Lucifer's cage and Dean on the outside alive and alone. While Castiel was able to resurrect Bobby and heal Dean, the elder Winchester was still devastated that God allowed Sam to remain locked in Lucifer's cage even though they did what was asked of them.

6 Death's Door (07.10)

The 10 Most Heartbreaking Supernatural Episodes

If Dean and Sam dying were not enough to make people cry anymore after 100 times, the death of other characters -- ones that won't come back -- still wreck the biggest Supernatural fans. In season 7, one of the most beloved characters on the show died when Bobby Singer finally met his demise.

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The episode was "Death's Door" and losing Bobby was probably even tougher for the boys than losing their own dad. Unlike John, who kept his sons at arm's length for their own safety, Bobby was there for them and kept them together and strong. The episode was even more heartbreaking because it took the viewer through Bobby's memories and we saw how much he really loved the brothers.

5 Sacrifice (08.23)

The 10 Most Heartbreaking Supernatural Episodes

"Sacrifice" was the season finale for Supernatural season 5 and while it didn't end up with a major death, there was almost one and it ended up as heartbreaking as any Sam or Dean death prior to this moment. Sam was trying to complete three trials in order to close the gates of Heaven.

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However, Dean soon learns from Naomi that Sam will die if he completes the three trials. In no surprise, Sam seems ok with that and the heartbreaking moment came when he told Dean that he believes he is a screwup and that Dean would be better with anyone other than him -- something Dean sets straight, strengthening their relationship and saving Sam's life.

4 Do You Believe in Miracles (09.23)

The 10 Most Heartbreaking Supernatural Episodes

While Dean has died over 100 times, when done right it can still rip our hearts out and stomp on them after doing it. In "Do You Believe in Miracles," it was yet another season finale where a Winchester brother died -- and this was Dean once again. The season saw Dean struggling throughout thanks to taking on the Mark of Cain.

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The big bad this season was Metatron and there was no way that he would make it to the end alive. However, the shocking moment came when Metatron drove the Angel Blade right through the heart of Dean -- in front of Sam. While Sam was heartbroken, it only got worse as Dean woke up as a demon -- the new Knight of Hell.

3 Dark Dynasty (10.21)

While they were not the best villains -- to say the least -- the Styne Family did something unforgivable. Dean and Sam were after Elden Styne and his family and needed to find a way to stop them and recruited Charlie to work with Rowena to decipher the Book of the Damned.

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By this time, Charlie (Felicia Day) had become a beloved fan favorite and helped the boys on many missions before this. However, "Dark Dynasty" marked the end of the road for the character when she finally cracked the book. However, Eli Styne found her and when Sam and Dean finally arrive at the motel, Charlie was dead in the bathtub and the Winchester brothers realized there was nothing they could do to save her.

2 Who Are We (12.22)

The 10 Most Heartbreaking Supernatural Episodes

Much like Supernatural season 5, the 12th season of the show pulled no punches when it came to heartbreaking moments. Plus, the toughest moments happened in the final two episodes of the season. In "Who Are We," the American hunters and British hunters battle reared its ugly head.

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Mary was under the control of the British Men of Letters and was just going around killing American hunters. When Mary was finally captured by Jody, Dean was able to get inside of his mom's mind. He found that she wanted to remain trapped in her mind because it had her happy memories and Dean told her that he loved and also hated her, bearing his soul and finally pulling her out and into action once again. Seeing Dean so hurt and vulnerable is always hard to watch.

1 All Along the Watchtower (12.23)

The 10 Most Heartbreaking Supernatural Episodes

Supernatural loves to leave viewers with very sad moments when it ends each season and the 12th was no different. After the touching moment in the previous episode where Dean bared his soul to his mother for everything she put him through by striking the deal with a demon and leaving them, all hell broke loose in the finale, "All Along the Watchtower."

The battle went into the rift where Team Free Will took the battle to Lucifer. Nothing ever goes as planned and the Winchester boys lost almost everything here. Crowley took his own life to close the rift but Lucifer followed them back through and killed Castiel in front of Sam and Dean. That was horrible but even worse was when Mary rushed Lucifer, knocking him back through and going through herself -- leaving Sam and Dean alone once again.

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