Over its 15 seasons, Sam and Dean Winchester (Jared Padalecki and Jensen Ackles, respectively) have had to say goodbye to one another and to family and friends too many times. So perhaps it was only fitting that Supernatural‘s ending had one last one for the brothers. But this one was the most heartbreaking of them all, because it wasn’t something they could have seen coming. There was no ticking clock, no warning. Instead, a hunt just went terribly wrong.
In honor of the final episode and that moment, we’ve gathered some of the emotional farewells the Winchesters and their family and friends have shared over the years below.
Dean Went to Hell (“No Rest for the Wicked,” Season 3, Episode 16)
After Dean sold his soul to bring Sam back to life, the clock was ticking…and when a year was up, hellhounds came to drag him to hell. The brothers tried to find a way out of it, but there was nothing they could do — and they didn’t even have the chance to really say goodbye (but just look at their faces at the beginning of the clip above). (But hey, it would only take until the Season 4 premiere for Misha Collins’ Castiel to grip Dean tight and raise him from perdition.)
Ellen & Jo’s Deaths (“Abandon All Hope,” Season 5, Episode 10)
“See you on the other side,” Dean told Jo (Alona Tal) before kissing her as, mortally wounded, she prepared to go out by blowing up hellhounds. But her mother, Ellen (Samantha Ferris), stayed with her, sacrificing herself as well. “I will not leave you here alone,” she said, before instructing Dean to “Kick it in the ass,” the catch phrase of the late producer and director Kim Manners.
Sam Went to Hell (“Swan Song,” Season 5, Episode 22)
It was all in the looks (again). After regaining control of his body from Lucifer, Sam took him and Michael (possessing the Winchesters’ half-brother Adam, played by Jake Abel) to hell. Dean, having been beaten by the devil, could only watch.
Bobby’s Death (“Death’s Door,” Season 7, Episode 10)
“Idjits” has never sounded so heartbreaking. Sure, it wouldn’t be the last time the boys saw Bobby (Jim Beaver) and another world’s version would eventually become an ally, but at the time, Sam and Dean lost a very important father figure.
John Returns to the Past (“Lebanon,” Season 14, Episode 13)
After a spell brought John Winchester (Jeffrey Dean Morgan) to the present from the past, he had to go back — and that meant saying goodbye to his wife Mary (Samantha Smith), and sons Sam and Dean. Prior to that, the four of them sat down for one family dinner with that upcoming separation hanging over them.
Rowena’s Death (“The Rupture,” Season 15, Episode 3)
Rowena (Ruth Connell) sacrificed herself for a spell to bring the ghosts and demons back to hell and, because of her death book, it had to be Sam that stabbed her. The others could only watch as she turned with a “Goodbye, boys,” before falling down to hell.
Castiel’s Sacrifice (“Despair,” Season 15, Episode 18)
With Death (Lisa Berry) determined to kill Dean and himself, Castiel summoned the one thing that could stop her: the Empty. But in doing so, he had to sacrifice himself, per the deal he’d made, and with a very emotional, very moving goodbye to Dean, he did just that.
Dean’s Death (“Carry On,” Series Finale)
What seemed like a routine hunt ended up being anything but, when Dean suffered a fatal injury and knew there was nothing that could be done. “I’m so proud of you, Sam. You know that? I’ve always looked up to you,” he told his brother before admitting that he’d stood outside his dorm “for hours” when he came to get him from Stanford way back in the pilot.
“I thought you’d tell me to get lost, or get dead. And I didn’t know what I would’ve done,” Dean explained. “I was scared. Because when it came down to it, it was always you and me. It’s always been you and me.”
“I love you so much,” he said. “My baby brother.” And he only died after Sam told him it was OK. Yes, they’d eventually be reunited in Heaven, but this was still the most tear-jerking scene of the entire series.
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