Dean Winchester’s whole life was chock full of suffering and pain in Supernatura, illustrated by a slew of quote that bring tears to the eyes of fans.
For all the joy Supernatural continues to bring to its loyal and passionate fandom, it brings them just as much pain with fifteen seasons worth of heartbreaking moments, deaths, and quotes. Not least of all these sad quotes come from Dean Winchester, someone whose whole life was full of suffering and pain, illustrated by a slew of lines that bring tears to the eyes of fans.
When He Breaks Down Asking John For Help
“I Need Your Help, Dad.”
For a good chunk of season 1, Dean is shown to be someone who does not let his emotions get the best of him, and one of the first proper times fans get to see the more vulnerable side of him is in “Home” when he phones his father.
Dean gets teary-eyed as he secretly phones John away from Sam – still keeping a front for his little brother – and tells his dad he does not know what to do and needs his help. Knowing the love and respect Dean had for John makes this small moment so impactful.
When He Loses Sam For The First Time
“What Am I Supposed To Do?!”
One of the most heartbreaking deaths in Supernatural is the first time Sam is killed in “All Hell Breaks Loose: Part 1” as Dean holds him and heartbreakingly says, “I’m going to take care of you; I’ve got you, that’s my job, right? Watch after my pain in the ass, little brother.”
Just as heartbreaking is at the start of part 2 when Dean sits with Sam’s lifeless body contemplating what to do and how to save him. Getting incredibly emotional, Dean comments on how he lets everybody down and how he cannot let Sam down. It is heartbreaking hearing Dean’s self-loathing at the best of times, much more so when Sam lies dead beside him.
When He Finally Scolds Mary
“I Hate You. And I Love You.”
Season 12 is arguably one of Supernatural’s worst seasons, but it gives fans some great stuff, including one of the most emotional sequences ever between Mary and Dean.
Trying to bring her back to reality and break the hold the British Men of Letters have over her mind, Dean tries to talk to Mary, letting out decades worth of baggage on her, something fans feel she sorely deserved. That line from Dean where he says he both loves and hates her will make the strongest of fans shed a tear.
When He Tries To Remember Who He Is
“My Name Is Dean Winchester. Sam Is My Brother. Mary Winchester Is My Mother. And Cas Is My Best Friend.”
One of, if not the best, episode of season 12 is “Regarding Dean,” where Dean falls victim to a memory curse that means he begins slowly but surely losing his memory.
The episode is a masterclass from Jensen Ackles, and the best yet the most heartwrenching scene is when Dean is alone staring into a mirror trying to retain his memories. Using Sam, Cas, and Mary, he desperately tries to cling on to who he is, getting emotional while doing so. It is beautifully done but painful to watch.
When He Says His Final Goodbye
“Don’t Leave Me…” “…Goodbye Sam.”
For all the issues surrounding the series finale of Supernatural, “Carry On” is so intensely emotional as fans say goodbye to the Winchesters, and they say goodbye to one another.
Dean undoubtedly deserved better than the death he got. However, those final lines exchanged between the two before Dean did die are arguably the show’s most emotional ever, as Dean accepts the fate he frustratingly believed he deserved and allows Sam to live a life without his big brother.