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The 20 Most Heartbreaking Moments In 'Supernatural'

January 21, 2021 9.7k votes 753 voters 16.8k views20 items

List RulesVote 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 scenes from Supernatural that definitely broke the fanbase's hearts.

  • 1

    Bobby's Demise

    Photo: The CW

    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.

  • 2

    Dean's (Final) Death

    Photo: The CW

    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.

  • 3

    Ellen And Jo's Sacrifice

    Photo: The CW

    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.

  • 4

    Sam's Loneliness After Dean's Passing

    Photo: The CW

    In the series finale, following Dean's demise, Sam is seen starting life on his own. Although he goes through the same routine, Sam is a shell of himself as he roams the bunker alone in the deserted hallways. Sam is then shown sitting in grief as he remembers Dean and how his brother had made everything come to life for him. 

    Later, Sam enters Dean's room to remind himself of him, where he's unable to contain his grief and breaks down crying as his loneliness envelops him completely.