11 'Supernatural' Deaths That Still Hurt (PHOTOS)

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Supernatural deaths
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In My Time of Dying
David Gray/The CW

John Winchester (Jeffrey Dean Morgan)

The Winchesters have a tendency to try to trade their lives (and souls) for one another, as John did for Dean in the Season 2 premiere.

SUPERNATURAL
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Sam Winchester (Jared Padalecki)

The death might not have stuck in the Season 2 finale, but Dean’s reaction and speech over his brother’s body remains one of the most heartbreaking scenes of the series.

Supernatural Jo Ellen deaths
The CW

Ellen and Jo Harvelle (Samantha Ferris and Alona Tal)

The mother and daughter hunting duo sacrificed themselves — Ellen refused to leave Jo — to take out hellhounds in Season 5’s “Abandon All Hope.”

Death's Door
Michael Courtney/The CW

Bobby Singer (Jim Beaver)

Just because there’s another version of Bobby out there now doesn’t mean we don’t still miss this world’s Bobby, whom Dick Roman shot in the head in Season 7’s “How to Win Friends and Influence Monsters.”

Holy Terror
Diyah Pera/The CW

Kevin Tran (Osric Chau)

Just because we’ve seen Kevin since his death and know he has a place in heaven doesn’t make his loss any easier. He went from being a normal kid in advanced placement to a prophet to tragically killed by Gadreel when the angel was possessing Sam in Season 9.

Katie Yu/The CW

Charlie Bradbury (Felicia Day)

Charlie was the sister Sam and Dean never had, and she risked her life to help them pretty much from the moment they met. Sadly, that was also what got her killed in Season 10. We were happy to see the apocalypse world version of the character, but it’s just not the same.

The British Invasion
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Eileen Leahy (Shoshannah Stern)

Sam and Dean met Eileen while hunting the banshee responsible for her losing her parents and hearing. She’d return to help them when Kelly Kline was pregnant, but after accidentally killing one of the British Men of Letters, she was killed by Ketch in retaliation.

Patience
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Missouri Mosely (Loretta Devine)

Sam and Dean first met the psychic in Season 1 and memorably helped them deal with a poltergeist in their old home. She finally returned in Season 13 — only to foresee her death and keep quiet about it when she sent Dean and Jody (Kim Rhodes) to protect her family.

Game Night
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Mary Winchester (Samantha Smith)

In Mary’s case, both her deaths still hurt. It was her burning on the ceiling of Sam’s nursery that kickstarted Supernatural. Though Amara brought her back in the Season 11 finale, Jack (Alexander Calvert) accidentally killed her and there was no bringing her back in Season 14.

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Death is an old friend to the Winchesters (and those around them) on Supernatural.

Over 14 seasons (so far), Sam (Jared Padalecki) and Dean (Jensen Ackles) have both died multiple times and seen people who have become like family be killed more times than they can count. But that doesn't make losing any of these characters — or any of these death scenes — any easier to watch.

The 17 Most Memorable 'Supernatural' Guest Stars (PHOTOS)See Also

The 17 Most Memorable 'Supernatural' Guest Stars (PHOTOS)

The Winchesters have saved, hunted, and worked with familiar faces over the years of the family business.

Click through the gallery above to see which deaths still hurt even years later.

Supernatural, 15th and Final Season Premiere, Thursday, October 10, 8/7c, The CW