‘Supernatural’: These Deaths Are Some of the Show’s Biggest Tearjerkers

Heading into this final season of Supernatural, fans can expect to see dozens of familiar faces from seasons past. Some are living, some are not, but we all have had our favorites over the years. To that end, viewers should be prepared for the loss of some of Supernatural’s finest and brightest. Until we get there, here’s a look back at some of the deaths that stung.

Jensen Ackles in Supernatural
Jensen Ackles in Supernatural | Dean Buscher/The CW

Bobby Singer

Like many of the characters on this show, Bobby has died more than once. But the most gut-wrenching death we’re talking about is the last one at the hands of Dick Roman. Remember that? It was stretched out over two episodes, where in the first the Leviathan chief shot him, and in the second, viewers walked through Bobby’s old memories and along with Sam and Dean, said a teary, unforgettable goodbye.

That is until he showed up eventually as a poltergeist and resident of an alternate universe, and we had to do it again.

Jo Harvelle, Ellen Harvelle

Jo and her mom Ellen were some badass hunters whose family was tight with all the Winchesters. Back in season 5, mom and daughter linked up with the brothers and Castiel to fight Lucifer and stop the apocalypse. Eventually, they had to go up against some hellhounds, and one wounded Jo. She died in her mother’s arms.

Ellen sacrificed herself by blowing up the building they were holed up in, but she bought enough time for Sam and Dean to escape. Somewhere in there, Dean and Jo shared a kiss and a tearful farewell.

Charlie Bradbury

Charlie—played by Felicia Day—was a fan favorite. Her third and final death was it, and not even the Winchesters could handle it. Season 10 saw Charlie return to help Dean with his Mark of Cain problem, and using her brilliance, she was able to crack the Codex. That Frankenstein dude killed her, and after the brothers found her body in the motel tub, they lost it. Later, Dean avenged her death.

Kevin Tran

We first met original Kevin and his mom Linda in season 7, and it was discovered he was the prophet. He spent a lot of time helping the Winchesters decode the tablets, but by season 9, Metatron had deemed him a threat. The bad angel enlisted Gadreel to kill Kevin, and he did so while he was possessing Sam’s body. This is one of the few times we’ve seen Dean brokenhearted, and fans were just as crushed.

This season, Kevin made a return to help the guys, and viewers learned that Chuck never sent him to Heaven; he sent him to Hell instead. Apparently, we might see more of dead Kevin.

Alicia Banes

Alicia Banes was/is the twin sister of Max Banes, two good witches/hunters that are the children of a witch and a hunter. They called on fellow hunters, the Winchesters, for help when their mom went missing. Their mother was killed by a witch and turned into a twig doll, and during an ill-fated rescue mission, Alicia was stabbed to death.

Max could not bear to lose both and broke down after his sister’s death. The Winchesters empathized but advised him not to do anything regrettable. He wound up using magic to turn her into a twig doll too.  

Benny

Benny the vampire was one of the coolest characters on Supernatural and one of Dean’s closest friends outside of Sam and Cass. He tried to make it work on Earth (but couldn’t) after escaping Purgatory with Dean, endearing himself to fans in the process.

He goes back to Purgatory—after Dean kills him—to help save Sam and stays behind so both Sam and Bobby can escape. He felt he belonged with the rest of the monsters, and part of Dean knew that. It was a sad parting.  

Mary Winchester

We know some fans were just fine with Mary Winchester being killed off in season 14, but the reaction of Jack, Sam, and Dean made it hard to swallow. The sight of her blighted ashes was too much for everyone. They lost their mother again.

Sam and Dean

The brothers have each died more than 5 times apiece, but that doesn’t mean each death hurt any less—for them or us. Perhaps fans are being groomed for the ultimate sacrifice when the show bows out this season.

Crowley

Oh, go ahead and admit it. By the time Crowley signed off, he grew on us, and became really close to Moose and Squirrel. Crowley went out like a b-o-s-s when he sacrificed himself in season 12 so the the boys could defeat Lucifer. His wit and get-it-done attitude is still missed.