These Heartbreaking 'Supernatural' Moments Remind You How Much You Miss It

These Heartbreaking 'Supernatural' Moments Remind You How Much You Miss It

Henry Adams
Updated January 2, 2025 36.6K views 15 items
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Vote up the scenes in 'Supernatural' that truly ripped your heart out.

There's no shortage of heartbreaking Supernatural episodes. Sometimes, characters would bottle up their feelings, then unleash their grief when they couldn't hold it in any longer. Other times, a sudden loss of a character or a character's friend or family member rocked the show's tight-knit fanbase. Whatever the reason, Sam, Dean, Castiel, and other main characters certainly succeeded in making the show's heartbreaking aspects stand out in our memories.

Here are the saddest and best scenes from Supernatural that definitely broke the fanbase's hearts.


  • 1

    Bobby's Demise

    Bobby's Demise

    In the Season 7 episode "How to Win Friends and Influence Monsters," Sam, Dean, and Bobby escape from Dick Roman but the latter manages to shoot Bobby. 

    In the episode "Death's Door," seconds before his demise, Bobby manages to regain consciousness after reliving a final memory of spending time with the boys. He remains alive long enough to call them "Idgits," his term of endearment for them, before passing and leaving Sam and Dean without their surrogate father.

    1,056 votes
    Heartbreaking?
  • 2

    Dean's (Final) Death

    Dean's (Final) Death

    In the series finale, after Dean and Sam finally defeat Chuck and get control of their lives, their happiness over their newfound freedom is shattered when Dean is slain on a hunt. In his final moments, he tells his little brother how much he loves him and asks Sam's permission to let him go. 

    Sam, in tears over the knowledge that this is the last time he'll be seeing Dean, relents and gives Dean his blessing to move on.

    1,074 votes
    Heartbreaking?
  • 3

    Ellen And Jo's Sacrifice

    Ellen And Jo's Sacrifice

    In Season 5's "Abandon All Hope..." Team Free Will goes after Lucifer, but are pinned down by a Hellhound. Jo becomes mortally wounded and asks the others to leave while she blows the place up to take the Hellhounds with her. 

    However, Ellen decides to stay with her daughter because she has no reason to live without Jo. Sadly, Ellen sees Jo perish in front of her eyes before she detonates the explosives, as the heroes suffer the heartbreaking loss of this mother-daughter duo.

    988 votes
    Heartbreaking?
  • 4

    Dean's Breakdown After Sam's Demise

    Dean's Breakdown After Sam's Demise

    In the second season finale, after Sam is slain by Jake, Dean takes his brother's body and is broken with grief. Admitting he has nothing in his life other than protecting Sam - which he's failed to do - Dean's initial sadness is turned into rage as it dawns on him that his reason for living has left him.

    At that moment, he decides he'd rather go to hell than live without Sam and heads off to trade his soul for his brother's resurrection.

    818 votes
    Heartbreaking?
  • 5

    Castiel's Declaration Of Love And His Sacrifice

    Castiel's Declaration Of Love And His Sacrifice

    In Season 15, episode 18, "Despair," Castiel and Dean are being pursued by Billie, who plans on slaying the two of them. Remembering that the Empty will take him when he experiences true happiness, Castiel decides to bare his soul and go with his heart.

    Simultaneously crying and laughing, he reveals he's been in love with Dean the whole time and urges him to remain the way he is because Dean isn't driven by anger, not to Castiel, but by love. A stunned Dean implores Castiel not to leave him, only for Castiel to place a hand on Dean's shoulder and cast him aside as the Empty arrives to take him - and also Billie - thus saving Dean's life as a smiling Castiel happily meets his end.

    903 votes
    Heartbreaking?
  • 6

    Dean Shares His Experience Of Hell To Sam

    Dean Shares His Experience Of Hell To Sam

    In Season 4's "Heaven and Hell," Dean finally confesses to Sam why he's burdened by memories of his time in hell. Not only did he get tortured every day for 30 years, but he was also the one who tortured others for 10 more years.

    Dean begins weeping as the memories of his victims return to him and he admits to Sam he hates how he enjoyed inflicting pain on people back then.

    770 votes
    Heartbreaking?