“Supernatural” is just one of those series that death strikes in every episode; however, some are more devastating than others. Here is a narrowed down list of the most heartbreaking deaths that have occurred, so far, throughout The CW hit. Obviously, for those who have yet to watch the show, spoilers are ahead. Lastly, it would have been easy to include Sam (Jared Padalecki), Dean (Jensen Ackles) and Castiel (Misha Collins), but seeing as they’re still alive and keep coming back, let’s focus on those that are actually dead and buried.
11. Jessica Moore
Fans really didn’t get a chance to know Sam’s Season 1 love, Jessica (Adrianne Palicki). In the Pilot, Yellow Eyes aka Azazel murdered Jessica right in front of Sam’s eyes, and he didn’t take it lightly. Audiences probably didn’t have a problem bidding Jessica farewell, but for those who adore Sam their hearts broke for the younger Winchester and his turmoil. Ever since her death, Sam just hasn’t been able to maintain a stable relationship, but who could as a supernatural hunter?
He only appeared in a few episodes, but Balthazar (Sebastian Roche) slowly grew on viewers as an angel of Heaven. First, a loyal follower of Castiel’s crusade in Season 6, he quickly betrayed Cas by giving up his secret location with Crowley to Sam and Dean. After discovering Balthazar was taking on Judas-like qualities, Cas killed Balthazar with really no hesitation whatsoever.
9. Victor Henriksen and Nancy Fitzgerald
They became victims just like every other victim, but it was extremely sad when these two died - probably because Sam and Dean went above and beyond to save them. Despite FBI Agent Victor Henriksen’s (Charles Malik Whitfield) goal to put the Winchesters behind bars he quickly realized they were sane and helped them. As for Nancy (Aimee Garcia) aka the virgin, she was a nice girl that happened to be in the wrong place at the wrong time. Lilith just couldn’t leave well enough alone and killed these two innocent souls.
Ash (Chad Lindberg) was a fun guy who could definitely pull off the “business up front, party in the back” mullet. At first glance, he didn’t look like the brightest crayon in the box, but he was a computer genius who provided Sam and Dean with all types of information. Unfortunately, he died in Season 2 when Harvelle’s Roadhouse was burned to the ground.
7. Pamela Barnes
A friend of Bobby’s (Jim Beaver), Pamela (Traci Dinwiddie) was a brilliant psychic who tried to find out what pulled Dean out of Hell. Consequently, she was blinded while communicating with Cas, but that’s not what killed her. Once again, events took a devastating turn when Pamela helped Sam and Dean visit the astral plane. While waiting for them, a demon got the advantage and stabbed her. She managed to safely retrieve both Winchesters, and before dying, she cursed Bobby for bringing them into her life, and warned Sam no good would ever come from his demon blood drinking ways.
6. The Trickster/Gabriel
Oh, The Trickster and/or Archangel Gabriel (Richard Speight, Jr.). Where to begin? He started out as the annoying creature who liked to play tricks on individuals in Season 2, but it was Season 5 where fans learned his true identity. At first, he believed Sam and Dean should willingly become the vessel’s for Lucifer (Mark Pellegrino) and Michael, but eventually he teamed up with the hunting duo in “Hammer of the Gods,” which ultimately led to his death by Lucifer (Mark Pellegrino).
5. Rufus Turner
As an old friend and hunting partner of Bobby’s, how couldn’t you like Rufus (Steven Williams)? He was rough, tough and got the job done. His demise came as a shock, especially when it was caused by Bobby. Well, it wasn’t technically Bobby, but an evil worm created by Eve that slithered inside Bobby. Nonetheless, it was a sad day for fans, and when Bobby realized what happened.
Who would have thought a vampire could become so loveable? He might not have been on the ins with Sam, but Benny (Ty Olsson) was Dean’s Purgatory wingman and helped the older Winchester brother survive. As hard as Dean tried to protect Benny, he had to gank him - and Benny was fine with it - near the Season 8 end, in order to extract Sam from Purgatory. Benny managed to rescue Sam - and Bobby - from the monstrous realm. He was last seen being attacked by fellow vamps.
3. Jo and Ellen Harvelle
They were the mother-daughter duo of the series who made a nice bond with the Winchesters. Jo (Alona Tal) and Ellen (Samantha Ferris) met their match on a trip with Dean and Sam to stop Lucifer. They both suffered devastating deaths with Jo putting herself in harms way to protect Dean, and Ellen blowing up herself, and her dead daughter, to kill evil hellhounds.
2. John and Mary Winchester
Mary’s (Samantha Smith) death was where it all started for the Winchester men, especially John (Jeffrey Dean Morgan). Just like Jessica, she died a tragic death, thanks to the Yellow-Eyed Demon. After that, John made it his life's work to kill the demon, and brought his boys along for the ride. Before ganking his wife’s killer (don’t worry, Sam and Dean got him), John sacrificed himself for a dying Dean by making a deal with Yellow Eyes - his life for his son’s.
1. Bobby Singer
Hearts are still breaking over this unexpected and gut wrenching death. Bobby Singer, who was more of a father to Sam and Dean than John, was shot in the head by Leviathan Dick Roman (James Patrick Stuart). He died, but did not cross over, and rather chose to remain a ghost. After becoming too vengeful, he gave Dean and Sam permission to burn his flask (a talisman) and bid them farewell. Bobby surprisingly appeared in Season 8, and Sam moved his soul from Hell to Heaven.
Whose death are you still bitter about?