Supernatural is known for its heartbreaking moments that never fail to bring tears to the eyes of fans. As the series progressed, the violence and devastation intensified, but viewers remained captivated by the Winchester brothers' journey as monster hunters. Although characters died frequently in Supernatural, the sadness never dwindled.

Sam and Dean Winchester's lives were a constant cycle of misery, loss, and sacrifice, which made the show incredibly addicting, offering an escape from the real world for a short while.

Among the many tear-jerking scenes in Supernatural, a few stand out as particularly poignant. In the very first episode, "Pilot," the deaths of Mary Winchester and Jessica Moore, decades apart, are tragic and heartbreaking. Sam's initial reaction to Jessica's death is enough to move anyone, but upon rewatch, the knowledge of the hardships awaiting the Winchester brothers deepens the sense of compassion towards them.

John Winchester, despite being consumed by his desire to avenge his wife's death, proved his love for his sons when he made a deal with Azazel to save Dean from a fatal car crash. John's sacrifice resulted in his damnation, leaving the Winchester brothers with a devastating loss. Another heart-wrenching moment occurs when Sam has to kill Madison, a werewolf he has formed a connection with. Having already lost Jessica, Sam is forced to end the life of someone he cares for and believes he could have had a future with.

While Sam and Dean die multiple times throughout the series, the first time Sam dies in Season 2 hits particularly hard.

Sam's unconsciousness allows fellow hunter Jake Talley to fatally stab him, ultimately resulting in one of the most emotionally charged scenes in the show's history. Dean is overwhelmed with guilt and proceeds to make a deal with Azazel, unable to cope with the loss of his brother.

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