There are moments in Supernatural that are so sad that they make fans of the show cry every time. The series got progressively more violent and devastating each season, but viewers were hooked to the drama, unable to stop watching. Dean and Sam Winchester endured so much over the course of their lives and were on the point of giving up so many times, but they never lost sight of their duty as monster hunters.
Supernatural characters died so often that fans lost count, but that doesn’t mean they weren’t sad every time. Sam and Dean’s lives were full of misery, loss, and sacrifice, and that is what made the show so addictive — it was easy to get lost in the Winchesters’ problems for an hour or two instead of dealing with what was going on in the real world. Still, some of Supernatural‘s saddest scenes hit differently than others, causing fans to cry their eyes out.
15 Mary & Jessica Are Killed (Season 1, Episode 1)
Even though “Pilot” is Supernatural’s first-ever episode and its viewers haven’t gotten attached to the characters yet, seeing Mary Winchester and Jessica Moore suffer the same fate decades apart is too tragic to bear. Sam’s initial reaction to his girlfriend’s death is enough to make anyone weep, but this scene causes so much more distress upon the next rewatch. Knowing what is to come next, audiences can’t help but feel compassion for the Winchester brothers.
14 John Saves Dean (Season 2, Episode 1)
John Winchester is hardly Supernatural’s father of the year, as he was so consumed with his desire to find whatever killed his wife, he forgot to actually raise his children, leaving them to care for themselves. Yet, John loves both his sons, even if he doesn’t always show it, and he proves just how much when he realizes that Dean is about to die from his car crash injuries and makes a deal with Azazel. John goes to Hell for a century so that Dean can live. The boys lose their father for good, and that’s only the devastating beginning.
13 Sam Has To Slay Madison (Season 2, Episode 17)
The early seasons of Supernatural destroy the viewers’ souls in a special way: giving the brothers one-off love interests they have solid chemistry with and then dramatically killing them off. That is the case with Madison, who turns out to be a werewolf. Having developed a connection with the younger Winchester, Madison asks Sam to kill her before she can endanger anyone. Sam isn’t over losing Jessica, and now he has to slay the first girl he likes and thinks he has a future with. That is too much to handle.
12 Jake Stabs Sam (Season 2, Episode 21)
Sam and Dean die many times throughout Supernatural, but nothing hits quite like the first time. In the season 2 finale, Sam unwillingly enters Azazel’s Hunger Games and comes very close to winning, rendering Jake Talley unconscious. Unfortunately, Jake wakes up and fatally stabs Sam, resulting in one of the most tear-jerking scenes in the show’s history. Sam dies in Dean’s arms, and the latter can’t deal with the guilt over failing to protect Sam, making a horrible deal with Azazel the very next episode.
11 Mary Shares Her Deepest Desire (Season 4, Episode 3)
In Supernatural season 4, Castiel sends Dean back in time, and he meets his parents there and discovers that monster-hunting has actually run in the family for longer than he knows. Dean talks to his mother, who admits that she wants to get out of hunting and have a family. This is followed by Mary’s prophetic words that she will try to do everything in her power to have her children raised away from hunting — Dean is barely able to hold back tears, and so are viewers.
10 Dean Talks To Sam About Hell (Season 4, Episode 10)
Dean’s Hell storyline is rightfully one of the most painful to watch in the whole series, and it is impossible not to cry during the scene where Dean finally confesses his “sins” to Sam. Dean has nightmares about his time in Hell, as he remembers how he was tortured and then how he was the torturer who lowkey enjoyed his job for the time being. Dean regrets feeling like this, unable to forgive himself, and Sam looks completely lost.
9 Ellen & Jo Sacrifice Themselves (Season 5, Episode 10)
Ellen and Jo Harvelle, the iconic mother-daughter duo, have the most unfairly brutal ending in Supernatural. The two women join Sam and Dean on their mission to take down Lucifer, and that proves to be the end for them. After Jo sustains fatal injuries, Ellen decides to stay with her daughter and blow up a bomb that would kill the hellhounds. In a devastating scene, a tearful Ellen hugs Jo’s body and pulls the trigger, sacrificing her life to save the Winchesters.
8 Lisa & Ben Forget Dean (Season 6, Episode 21)
Lisa and Ben Braeden are Dean’s found family that he sadly has to say goodbye to in Supernatural season 6. Following a demon’s attack and possession of Lisa’s body, Dean asks Castiel to erase Lisa and Ben’s memories of him to keep them out of danger. When Castiel heals Lisa’s wounds and deletes every trace of Dean, the latter comes into her hospital room to check up on her, pretending to be a stranger. Ironically, watching Dean realize that neither Lisa nor Ben remembers him is unforgettable.
7 Bobby Singer Dies (Season 7, Episode 10)
Bobby is a better father to Sam and Dean than John ever was, as he is the one who basically raised them and was always there for them. In Supernatural season 7, Dick Roman, the leader of the Leviathans, shoots Bobby into a state of coma, and the nostalgic episode hits viewers right in the feels. Bobby’s life is shown in the flashbacks, courtesy of the reaper, and Bobby himself is desperately trying to wake up long enough to get a vital message through to Sam and Dean. He manages to do it, calls them “idjits” one last time, and passes away.
6 Dean Learns That Kevin Is Dead (Season 9, Episode 9)
In Supernatural season 9, another unexpected low blow comes to the Winchester brothers. Unaware that Gadreel is Metatron’s ally, Dean allows him to possess Sam’s body, which he uses to kill Kevin Tran, the Winchesters’ longtime partner and friend. Having lost both his brother and Kevin to Gadreel, Dean can’t deal with his own guilt over what has just happened. Seeing him just quietly sit there, crying and uttering Kevin’s name, shattered fans’ hearts to pieces.
5 Eldon Murders Charlie (Season 10, Episode 21)
Сharlie Bradbury is a foster sister to Sam and Dean, so losing her after having lost so many others hits right where it hurts. In Supernatural season 10, the Winchesters face the Stynes, who want the Book of the Damned back, and they are willing to do anything to get it. Sam and Dean ask Charlie to decode the Book, and she ends up getting caught in the crossfire. Eldon Styne finds Charlie and violently murders her in her motel bathtub off-screen. When Sam and Dean discover her body, they are distraught, and so are viewers. In fact, Supernatural fans were downright angry about Charlie’s death.
4 Dean Forgets Who He Is (Season 12, Episode 11)
Supernatural season 12, episode 11, “Regarding Dean,” leaves Dean grasping at straws after a witch curses him, and he starts losing his memory. The episode starts out with lots of fun sequences, but things take a grave turn soon after when Dean’s memory quickly deteriorates. The scene where Dean’s identity is slipping, and he keeps repeating his own name and the names of the people he loves, is on another level of acting skill, and it is impossible for viewers not to shed a few tears during the moment.
3 Sam Is Forced To Kill Rowena (Season 15, Episode 3)
Rowena is the Winchesters’ most unlikely ally. They have a difficult relationship over the course of Supernatural, but they grow to love each other. In season 15, Rowena is helping Sam and Dean with a particularly morbid spell that requires a human sacrifice. After all the other options go out the window, Rowena decides to give up her life for the spell to work and chooses Sam, her favorite, to be the one to kill her. A heartbroken Sam hugs Rowena and stabs her, cranking up the drama and causing viewers to cry their eyes out.
2 Castiel Makes The Ultimate Sacrifice (Season 15, Episode 18)
Supernatural’s final season is an emotional rollercoaster from start to finish, and Castiel’s death is something fans are still bitter about. In an attempt to save him from Death, Castiel confesses his love to Dean, letting the Shadow take him and finish Billie in the meantime. This is the moment viewers craved for years, and while it is incredibly dramatic, having Castiel die right after his big revelation feels underwhelming, to say the least, so there are two reasons to sob over the scene.
1 Dean Dies For Good (Season 15, Episode 20)
There isn’t a single Supernatural viewer who thought that the finale wouldn’t obliterate them, and yet no one was prepared for what took place. Dean’s words about going out in a fight turn out to be a self-fulfilling prophecy, and he dies in Sam’s arms, finishing his long, tiresome hunting journey. Crushed by Dean’s irreversible death, Sam says goodbye and holds his brother’s body close to him. This ending makes a lot of sense for Dean, but it still doesn’t feel even a little bit fair.
