Tears from the fans are not something that is rare on Supernatural, a show that is chock full of loss and heartbreaks throughout its fifteen seasons, coming to an end in 2020 after a fifteen-year run that has left its dedicated fandom an emotional wreck.
Fans have seen beloved characters die, some of 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 some of the most heartbreaking Supernatural episodes.
Updated on February 13th By Rhys McGinley: Supernatural has a knack for taking the emotions of its fandom and twisting them, bringing immense pain and sadness to those who adore the show in and amongst all of the brilliance it gives. Limiting heartbreaking Supernatural episodes to a list of ten does not do justice to just how many times the show broke our hearts over the course of its fifteen seasons, from the very start to the very end, whether it be through deaths, touching scenes, or even colossal endings.
"Heart" (02.17)
A constant in Supernatural is the idea that Sam and Dean, and hunters in general, find it nearly impossible to escape the life, to have an everyday, apple pie life, to have love, with romances coming and going through all fifteen seasons.
One of Sam's first romantic sparks post-Jess was Madison, who in "Heart," turned out to be a Werewolf. Despite their best attempts to help her, Sam and Dean could not save Madison, leading to her begging for death, with Sam making the gut-wrenching decision to kill her.
"In My Time of Dying" (02.01)
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.
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.
"All Hell Breaks Loose" (02.21)
Not only did season 2 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.
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 Sa,m 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.
"No Rest For The Wicked" (03.16)
While the start of season two almost brought the death of Dean, season three brought it to fruition with one of Dean's most brutal deaths in his career of dying.
Despite a slew of attempts to fight off Lilith and the impending year left on his life coming to an end, Dean, along with Sam, Bobby, and Ruby, failed. Dean is torn apart by Hellhounds, and fans get their first glimpse of hell as Dean is chained up bloody and battered, screaming for his brother.
"Dark Side of the Moon" (05.16)
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 multiple heartbreaking Supernatural episodes.
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.
"Abandon All Hope" (05.10)
With fifteen seasons and over three hundred episodes, Supernatural is filled to the brim with characters who have impacted Sam and Dean's lives, but in the Kripke era, few were as loved as Ellen and Jo.
"Abandon All Hope" sees the heroes prepare for a showdown with Lucifer, trapped by hellhounds by Meg in a town rife with Reapers waiting for death. With Jo severely injured, the mother and daughter decide to stay behind and sacrifice themselves to save the brothers, killing the hellhounds in the process, A true tear-jerker.
"Swan Song" (05.22)
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.
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.
"Death's Door" (07.10)
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.
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.
"Sacrifice" (08.23)
"Sacrifice" was the season finale for Supernatural season 8, 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.
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.
"Do You Believe in Miracles?" (09.23)
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.
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.
"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.
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.
"Who Are We?" (12.22)
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.
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.
"All Along the Watchtower" (12.23)
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 a 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.
"Despair" (15.18)
The entire ending of Supernatural is highly controversial in the dedicated fandom, and so many people were hurt by how the last few episodes played out. But, there is no denying the heartbreak they invoke in the fans.
"Despair" caused just that. This episode ends with not only the entire world vanishing with the exception of Jack and the brothers as ways to defeat Chuck become scarcer by the moment but an admission of love and final goodbye to one of Supernatural's most adored characters, Castiel. The final moments Cas and Dean share are gut-wrenching and tear-inducing, and it is one of the hardest goodbyes fans of the show have ever faced.
"Carry On" (15.20)
Of course, with a show as beloved, with as dedicated fandom, and such longevity as Supernatural, there was always going to be one goodbye that was harder than the rest, that, of course, being the final goodbye.
"Carry On" undoubtedly has some moments for fans to cling to, but it is an insanely divisive and criticized episode for the way it disrespects many characters. Nevertheless, Dean's final death, his car ride in Cas and Jack's heaven blasting the greatest song of all time, "Carry On Wayward Son," and the final reunion between the brothers will likely never fail to reduce fans to tears. The brothers are done; they have peace.