Top 10 Saddest Supernatural Moments
#10: Ellen & Jo’s Deaths “Abandon All Hope...”
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Ellen and Jo Harvelle were a mother and daughter who ran a saloon that often catered to hunters of the supernatural. Frequent allies and a kind of pseudo family to Sam and Dean, Ellen and Jo join the boys on an incredibly dangerous mission to kill the Devil. During a hellhound attack, Jo is mortally wounded. Hoping to buy time to give the brothers a shot at Satan, Ellen remains behind with her dying daughter and offers to help set off a bomb to kill the pursuing hellhounds. As heroic as Ellen’s sacrifice was, the Winchesters (and fans) likely would have given anything to have the mother-daughter team live to fight another day.
#9: Dean Stops Sam’s Sacrifice “Sacrifice”
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Speaking of sacrifices, season 8 sees Sam Winchester undergo a series of trials and challenges with the end goal of closing Hell forever. Unknown to him and his brother though, the trials will lead to his death. After Dean learns this information from a morally questionable angel, he returns in time to stop Sam from completing the final trial. The most emotional part of the scene is the interaction between the brothers, as Sam reveals to Dean how much guilt he carries for the times he has let him down, which he feels led Dean to turn to others for help instead of him. Dean counters by telling Sam that his brother will always come first, no matter what.
#8: Dean’s Amnesia “Regarding Dean”
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An encounter with a witch leaves Dean cursed with a deteriorating memory. Although the situation is at first somewhat comedic, it later takes a tragic turn, as Dean slowly forgets more and more important details. This culminates with a scene of him standing in front of the mirror, repeating his own name and the names of those closest to him in a fruitless attempt to hold on to his identity and his feelings for those he loves. Jensen Ackles’ acting is in fine form; he expertly conveys Dean’s internal struggle and the distress it’s causing him, making for a heartbreaking viewing experience.
#7: Castiel Nearly Kills Dean “Goodbye Stranger”
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Despite how close they are, Dean and the Winchesters’ favorite angel, Castiel, sometimes end up coming to blows. While Dean beating up Cas under the influence of the Mark of Cain is pretty tough to watch, we ultimately went with a moment that saw Cas as the aggressor. After locating an angel tablet written in the word of God, Castiel is taken over by the angel Naomi, who forces him to attack Dean. Watching Cas break Dean’s arm and beat him to a bloody pulp is tough to sit through, but the thing that hits us, and Castiel in the feels the most, is Dean’s plea to snap out of it; calling Cas his family and telling him how much he needs him.
#6: John Winchester’s Death “In My Time of Dying”
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The patriarch of the Winchester clan is a complicated figure, and his crusade to find his wife’s killer, a yellow-eyed demon, drags his sons into the world of monster hunting. Catching up with the demon nearly costs Dean his life though, so John makes a deal with his wife’s murderer to save Dean’s life at the cost of his own. Sam dropping his coffee cup in slow motion as he realizes his dad is dying is one of the show’s most powerful moments. While it’s an early death in the show’s run, it still resonates all these years later because of how much their father’s absence has affected both of the Winchester brothers - and the show as a whole.
#5: Charlie’s Death “Dark Dynasty”
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Another surrogate family member to the Winchesters, Charlie was like the nerdy little sister the boys never thought they wanted, but were definitely glad to have. While in conflict with the Frankenstein family over the Book of the Damned (yes, really), Charlie is called in to decode the text. Unfortunately, the Stynes eventually catch up to her, and though the Winchesters beg her over the phone to give Eldon Frankenstein what he wants, Charlie refuses. Eldon violently kills her offscreen, leaving the Winchesters and fans alike heartbroken when they find Charlie’s body in the bathtub of a motel.
#4: Castiel Bids Farewell to the Winchesters “Stuck in the Middle (with You)”
Many of the cast members of “Supernatural” have died at some time or another, but a moment needn’t be a fatal one to bring us to tears. In this season 12 episode, Castiel is stabbed with the Lance of Michael by a demon, which brings swift death to evil beings and a slow death to the good; leaving Castiel with a long, painful death indeed. With the demon closing in on them, Castiel tells the Winchester family that he loves them all and urges them to leave him, so that his last memory isn’t of them dying too. The only way this moment could have been sadder would’ve been if Cas hadn’t been saved from his fate. Are we ever glad he was!
#3: Dean’s Hell Confession “Heaven and Hell”
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After returning from Hell, Dean doesn’t exactly feel heavenly. During one of the Winchesters’ famous brotherly heart to hearts, he reveals that time moves faster down below and that he spent 40 years there. His demonic torturer offered to relent in his punishment if he would torture others. Although Dean was able to resist for 30 years, he eventually gave in and spent the last decade inflicting pain on others. Brilliantly acted, the monologue Dean delivers is absolutely heartbreaking and would easily be the saddest Dean moment in the series… if not for the next entry.
#2: Dean Loves & Hates His Mom “Who We Are”
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Season 12 sees the Winchesters finally reunited with their murdered mother. However, resurrection can’t undo decades of festering familial issues. Mary Winchester’s choices after coming back don’t exactly make it easy for the boys to forgive her, as seen when Dean kicks her out. Regardless, Dean is determined to snap her out of a dream world Mary finds herself in when she’s brainwashed, and to do it, he lays it all out – his hatred of her for making a choice that led to a lifetime of danger and heartache for her sons. Despite this resentment, Dean manages to forgive her, because he still loves her. Oof…so many feels! Before we get to our top pick, here are a few honorable mentions: Lisa & Ben Forget Dean “Let It Bleed” Benny Returns to Purgatory “Taxi Driver” Sam Figures Out Dean Sold His Soul “All Hell Breaks Loose: Part Two” Dean Calls Sam a Monster “When the Levee Breaks” Dean’s Death After Fighting Metatron “Do You Believe in Miracles?”
#1: Bobby’s Death “Death’s Door”
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Bobby Singer was among the Winchesters’ most stalwart friends and allies; acting like the father they always wished John Winchester could have been. So when Bobby is shot by the season’s villain and is on death’s door, it’s already pretty sad. But given that a reaper shows him a whole “this is your life” sequence in his final moments, which details his tragic origins killing his abusive father to protect his mother, while also illustrating his love for and pride in Sam and Dean… it made his last moments all the more heartbreaking. “Idjits…” We’re not crying, you’re crying!
