To kick things off, here is my official list of the Top 10 Best Manly Tears!
You may think this show is about a couple of brothers hunting down ghosts, monsters and demons while listening to classic rock in their '67 Impala, and you wouldn't be wrong. But it's just as much about the carefully placed manly tears. In compiling this list, I realized that despite Sam being the "sensitive" one, it is in fact Dean who cries the most tears throughout the series. Sam does a lot more teary eyes than actual tears, but when he does cry, it turns into a regular sob fest. Dean, on the other hand, specializes in that single teardrop down the cheek. It can sometimes turn into more if he's feeling particularly self-loathing, though. And we know he is so full of self-loathing most of the time, so get ready to cry yourself some manly tears along with the Winchesters! (By the way, I was going to embed all of the clips of these scenes, but only one of them let me have an embed code, so instead I have to link you and provide screencaps, which is taking way longer!!!)
10. John's funeral pyre
(2x02 "Everybody Loves a Clown")
After John abruptly dies at the end of the previous episode, the boys bid adieu to their dad in a funeral pyre - with his body salted too, naturally. The moment is mostly silent but for Sam asking if John told Dean anything before he died, to which Dean of course LIES before letting his one silent tear drop down his cheek. And guys, this is one of the only times where the guys actually cry at the same time. It hardly ever happens, and that's partially why this moment made it into the top 10 above some other options.
9. The boys have a final goodbye with their daddio
(2x22 "All Hell Breaks Loose - Part II")
Sam and Dean get some help from the ghostly form of their father, who has escaped from Hell thanks to the gate being open, to finally be able to kill Azazel (aka the yellow-eyed demon or YED for short). After he sputters and sparks dead to the ground, Dean and Sam have a final, silent, tear-filled goodbye with John before he sparkles away to points unknown. Another rare occasion where we see both boys cry at the same time! And I think John might've been sporting some tears as well. Triple tears!
8. Dean talks to John's grave
(2x20 "What is and What Should Never Be")
Dean gets to see what life would've been like had Mary never died thanks to a djinn. Although it seems like life is pretty good, he starts to realize that because John never raised his boys to be hunters, everyone they ever saved died. He goes to John's grave (because although Mary was alive in this world, John had still died, though not because of the yellow-eyed demon), and there asks why it's their responsibility to save everyone. Why can't they have a normal life? He wants it so bad, but eventually gives it all up to be the hero. That's our Dean.
7. Sam clutches dead Dean
(3x16 "No Rest For the Wicked")
Despite their best efforts, the boys were not able to prevent Dean from having the hellhounds drag him to Hell. While Dean is getting ripped to shreds right in front of him, Sam has to contend with Lillith, who tries to kill him with her white light hand thingy. It doesn't work, though, so she skedaddles before Sam can kill her. After she's gone, Sam's left alone with Dean, who's lifeless and torn to bits on the floor. As he laments his brother, we zoom in on Dean's dead eye, straight down into Hell, where he's strung up in chains and shouting for Saaaaaaammmmm!
6. Sam has to kill Madison
The boys think they have cured Madison of her werewolfiness, and Sam gets it on with her, only to find out that they didn't cure her after all. There's nothing they can do, so she asks Sam to kill her. Sam has a hard time with the mere idea of this, so Dean offers to do it for him. Sam says no, she asked him to. He grabs the gun, and before he goes to do it, he looks back at his brother, tears streaming down his face. Silent Lucidity is playing on the soundtrack and man, what a beautifully crafted scene. As Sam walks out to do the right thing, Dean lets one manly tear fall down his cheek, then flinches as he hears the gun shoot. These boys can never have any happiness.
5. Dean talks to dead Sam
(2x22 "All Hell Breaks Loose - Part II")
At the end of the first half of this two-parter season finale, Dean's worst fears come true - Sam is killed. Though Bobby tries to keep the sanity, Dean yells at him to get out, and has a one-sided chat with his dead little brother, about how he screwed up the one job he was supposed to do. That is, protect his Sammy. He is at a loss. "What am I supposed to do?!" As we know, he does something terrible that sets off a big chain of events leading to the apocalypse. Whoops.
4. Dean begs young Mary not to get out of bed
(4x03 "In the Beginning")
Dean travels back in time to when Mary and John were about to get engaged, and finds out that his mom was a hunter long before John ever started them down that path. In this chat, Mary confesses to Dean that she hates hunting and swears she will never raise her children in that life. Aw man, you can just see his heart breaking at her saying that. He then asks her please, no matter what she may hear, to not get out of bed on that fateful night in November 1983. He wants so badly for her to have the apple pie life she desires, that some manly tears flow.
3. Dean tells Castiel to find someone else
(4x16 "On the Head of a Pin")
When the angels force Dean to use the torturing skills he used in Hell to torture information out of Alastair, Alastair, instead of telling him who has been killing angels, informs Dean that it's his fault that the seals are being broken. When he started torturing in Hell, that was the first seal to break. After a subsequent major beat down by Alastair and near save by Sam, Dean has a chat with Castiel about what it all means. Cas says that the man who begins it is the man who must end it, but Dean is so broken down at this point he tells Cas to find someone else. GAH. I may start crying of sympathy just thinking about it.
2. Dean says he should be dead rather than John
(2x04 "Children Shouldn't Play With Dead Things")
After John mysteriously died and the Colt disappeared just after Dean miraculously recovered from injuries that would have killed him, the boys figured something fishy probably went on, though of course they don't actually talk about it for a while. While Sam is dealing with John's death, Dean has been bottling up his feelings about the whole thing, only to finally tell Sam what he's really feeling here in another of their patented roadside feelings chats. He feels like he should be dead rather than their dad, and there's nothing Sam can say to make that alright.
1. Dean confesses what he did in Hell
(4x10 "Heaven and Hell")
After Dean came back from Hell, he told everyone that he didn't remember what happened to him. It quickly became obvious that this was a bald-faced lie, but he wouldn't talk about it, despite Sam's many pleas for him to. Finally, after a confrontation with Alastair, Dean comes clean. And it's so much worse than Sam could have imagined. His pain, and his wish that he couldn't feel anything, is so heartbreaking that it almost makes Sam cry for him (but like I said, Sam's all about teary eyes rather than tears, so we only got the teary eyes here). In conclusion: DEAN! You have so much manly pain.
And there you have it. Do you agree with my choices, or do you think I missed a big moment? Vote below, and let me know in the comments if I made a glaring mistake!