The Most Heartbreaking Death In All Of Supernatural
Because so much of the 15-season run of "Supernatural" focuses on the drama of hunting down and killing everything from demons to werewolves, the series involves more than its fair share of death and destruction. From this show's first episode to its last, it routinely proves its willingness to push the boundaries of tragedy and despair.
Of course, in a show of this nature, quite a few of these "deaths" are actually only temporary. Indeed, death and resurrection come multiple times for many "Supernatural" characters — including Sam (Jared Padalecki) and Dean Winchester (Jensen Ackles), both of whom die and return repeatedly throughout the series, and their parents, Mary (Samantha Smith) and John Winchester (Jeffrey Dean Morgan), both of whom also meet similar fates.
Despite the fact that death is so commonly undone in "Supernatural," the loss of certain characters still understandably saddens some of the series' most dedicated viewers. For example, one particular fan-favorite character met his end in Season 7, leaving many fans in tears (via Reddit).
Bobby Singer's death takes more away from the Winchester brothers than any other
Bobby Singer (Jim Beaver) serves an important role in the Winchester brothers' lives for a great many years. In a world full of blood-sucking vampires, fire-breathing dragons, and vengeful spirits, Bobby is one of the precious few people the brothers can consistently count on for support, no matter the ask. Of course, this is part of what makes Bobby's death in Season 7 so heartbreaking.
Sadly, every life must come to an end, even in "Supernatural." In Season 7, Episode 9 ("How to Win Friends and Influence Monsters"), Bobby is shot in the head by the Leviathan, Dick Roman (James Patrick Stuart). He subsequently dies in Episode 10 ("Death's Door"), leaving Sam and Dean to mourn his loss. Interestingly, part of the reason that Bobby's death is so sad does not become clear until long after his actual passing.
Sam and Dean later encounter multiple other versions of Bobby, including Bobby in ghost form and Apocalypse World Bobby, a man they think they know, but who has no memory of them. Each appearance of Apocalypse World Bobby is sadly just another reminder of their loss. Unfortunately, the version of Bobby that serves as a father figure to the Winchester brothers is gone for good, simply relegated to spirit form for the foreseeable future.
Notably, series creator Eric Kripke might have still been mourning Bobby's loss when he wrote a "Supernatural" Easter egg into "The Boys" Season 2.