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.
Whether they be emotional declarations and moments with Sam, heartbreaking goodbyes, or Dean vocalizing the pain he tries so hard to bottle up, Dean Winchester has many sad quotes that break fans.
When He Did Not Realize People Wanted To Help
"What?"
This one-word quote from Dean comes as he justifies making a demon deal to save Sam in "All Hell Breaks Loose." After saying it was his job to look after his little brother, Sam responds shocked, saying, "And what do you think my job is?"
Dean's one-word whisper response of "what?" combined with the shock on his face is heartbreaking. Not for one second did he even consider the fact that anyone else would or would want to look out for him, much less the little brother he had spent his life protecting.
When He Finally Opens Up About Hell
"I Wish I Didn't Feel A Damn Thing."
When Dean returns from hell in season 4, he plays it off that he does not remember what the experience was like. Bottling that lie up did not last, however, and he eventually let Sam into the truth.
Telling him about the pain of being there and how he remembers it all, Dean heartbreakingly and famously says this line as tears drip from his eyes. It is painful to see a character fans adore so much in so much pain and riddled with so much undeserved guilt for the evil things Dean was forced to do against his true human will in hell.
When He Gives Up Lisa & Ben
"If You Ever Mention Lisa And Ben To Me Again I Will Break Your Nose."
It is almost an underappreciated tragedy in Dean's life that he had the apple pie life he wanted deep down, but did not get to keep it. How he gave them up for good by having Cas wipe their memories is one of the saddest Dean moments in the whole show.
What makes it worse is how much pain he bottled up regarding it but would never, ever let out. Fans cannot help but feel for Sam, who does just try to help but is hit by a threat by Dean, who never wanted to hear about his almost normal life again. After Ben and Lisa, Dean never came close to finding that type of happiness away from the life. While Lisa and Dean's relationship was arguably doomed from the start, Dean deserved better.
When He Refuses To Give Up On His Brother
"Sam, it's okay. It's okay. I'm here. I'm here. I'm not gonna leave you. I'm not gonna leave you."
"Swan Song" is widely regarded as one of, if not the best, episode of Supernatural's entire run, and is such a heartbreaking watch, particularly the climax involving Sam and Dean at the site of Michael and Lucifer's battle.
Both have some painfully sad quotes, and this line from Dean where he assures Sam that he will not leave him is just one of them. The mental and emotional strength from both brothers in the episode and this particular sequence is astounding, and for over a year, this was the last thing Dean got to say to Sam.
When He Loses Hope After Losing Everyone
"I Need You To Keep The Faith For Both Of Us. 'Cause Right Now I... Right Now I Don't Believe In A Damn Thing."
The start of season 13 may have been Dean's lowest point in all of Supernatural. There had been times where he had lost everyone and other times where he had given up, but never before this were the two combined to such a high degree.
Dean, and Sam too, lost Cas, lost Crowley (whose death ended up being permanent), and lost their mom, left to raise Lucifer's son by themselves, and Dean was not only broken by this but tired with life. Sam had to drag him out of the hole with help from Castiel's resurrection and the hope that Mary was alive. It was awful seeing the character so low.
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.