There is indeed so much brotherly angst that it was rather difficult to make this list. When I'm doing these top tens, my process is basically: write down all of the ones that come to my head first, then go through a list of all of the episodes and think on whether there were moments that could qualify, then from there try to narrow down which are the "best." Honestly, there's probably one moment from every episode in the entire series that could technically qualify, but hey, let's not make my head explode here. Usually the ones that come to mind first do so for a reason!
That being said, I do feel I am presenting this list with the most trepidation compared to the others. It seems very heavy in a couple of seasons, with one season being left out entirely. So feel free to have at it in the comments with the moments I missed! But for now, here is the list...
(Reminder: The title for each number is a link to a youtube clip of the moment I am addressing!)
10. Sam shoots Dean
While the boys certainly do a lot of disagreeing with each other in season one, and some arguing about John and whether they should follows his orders, this episode brought all of their tension to the forefront when Sam gets sort of "infected" by Dr. Ellicott, this evil ghost psychiatrist dude. Through the ghostly influence, Sam's pent up feelings toward Dean come raging to the surface, to the point where he even shoots him - once with rock salt, and well, the other is an attempted shooting with a real gun, but it wasn't actually loaded. The point is that he actually shot it, though! Sam! How rude. Though most of the scene features Sam berating Dean for always following John's orders, I think my favorite part of the scene is that part I have quoted in the above image, when Dean says, "You really hate me that much?" Awww. Dean just wants his little brother to love him!
9. Dean punches Sam
Truth be told, Dean punches Sam more than in just this episode, but this is the first time he does it, I'm pretty sure. And though his later punches are more directed at Sam specifically, this one was less about Sam and more about his anger and guilt over John being dead. Nevertheless, John's death creates quite a lot of tension between the boys, as some of the later moments will no doubt further reveal. In this particular moment, Dean has become rather taken with vampire hunter Gordon, to the point where he's trusting him more than he's trusting Sam. Sam gets fed up with it and tries to get through to him, so Dean naturally punches him rather than address his feelings. Ah Dean, there are other ways to express distress aside from punching. Of course, as we'll see, Dean's words can often hurt worse than his punches.
8. Siren fight
(4x14 "Sex and Violence")
Throughout season four, the boys grew distant toward each other, what with Dean dealing with what happened to him in Hell, and Sam doing his mind mojo to exorcise demons. At this point, Dean didn't even know he'd been drinking blood yet. And while the boys had done a good job at keeping their emotions about it mostly pent up, when under the influence of a siren, they finally got to let their real feelings about each other be known. Dean says that the Sam he knew is gone, basically insinuating that Sam's sort of becoming a monster, whereas Sam accuses Dean of being weak and holding him back from getting the job done. It even escalates to the point where the boys get into a battle of the fists! Luckily, Bobby comes to the rescue. Unluckily, the boys do not get to un-hear what they said to each other, and despite both of them claiming otherwise, it was clear they had both been speaking the truth. As we know, things only go downhill from here.
7. Sam's been using his scary demon powers after all
Before their feelings ever came to such a head, however, we first got a glimpse into the rapid destruction of the brothers' relationship when Dean found out that Sam had started using his demon powers again while Dean was in Hell. This gains Sam another classic Dean punch to the face and many more protestations about what he's doing, to the point where Dean basically says without saying that he thinks Sam's starting to become exactly what John had warned him about. Later in that same episode, Sam gets fed up with Dean and unloads on him how he's just trying to make the best of a bad situation. He seems to get through to Dean a little bit, but as we know, it is short-lived, mostly because neither of them really likes to listen to the other when they think they're in the right.
6. He told me something about you
At the beginning of season two, John whispers something into Dean's ear before he walks off to his untimely death. We finally find out just what he told him here, and it's definitely nothing good. Turns out, he told him that he had to save Sam, and that if he couldn't, he'd have to kill him. This has been weighing on Dean all this time, and he finally unloads it on Sam after it turns out that Sam is immune to the demon zombie virus in "Croatoan." Sam is appropriately pissed that Dean would keep such a secret from him, despite their dad's insistence on the matter, and even though it looks as though Dean convinces him to try and lay low for a while, it turns out that Sam takes off on his own. Sammy, you can't always just run away when you get upset with your family. But that was certainly his MO for quite some time.
5. Too little, too late
(2x02 "Everybody Loves Clowns")
After John abruptly dies in the previous episode, Sam suggests they go on a hunt, and gets rather gung-ho about the whole situation, even stating that he probably won't go back to school after they find the demon that killed their mom and Jess, which is a complete 180 from what he had previously been stating. Dean finally has enough and confronts him about how Sam is suddenly so loyal to what John wanted after he's dead when the last thing they ever really did was fight (which is what they nearly always did). This is particularly upsetting to Sam, as Dean is basically voicing all of the things he is unable to admit to himself. By the end of the episode, Sam does admit that he feels terrible about how things ended with John, but he also points out to Dean that he isn't handling it well either, despite what he may say, which will eventually lead to Dean punching him, as mentioned up in number nine above.
4. Sam's best moments are Dean's worst
(5x16 "Dark Side of the Moon")
In this episode, we find out that Heaven is a place where everyone gets to relive their best moments. While Dean's moments are all filled with being together with his family, Sam's are anything but. In fact, they turn out to be some of the worst moments of Dean's life. While Dean mostly lets this go by being passive aggressive for a while, it all comes to a head when they arrive at the point when Sam decided to leave John and Dean and go off to Stanford, which ranks as the worst night of Dean's life (the comics that show what happened to get them to this point purport that John also leaves Dean at the same time.. I'm not sure if this is true for the show, since it seemed in the pilot that Dean and John had been working together and John had only recently disappeared... but if it is true then well, no wonder it was the worst night of his life). Anyway, sorry for that digression. While Sam tries to make Dean understand that he has never viewed family the same way as Dean, Dean conversely wonders whether this means that he and Sam aren't really as close as he thought. Seeing as this whole season was about the brothers Winchester figuring out their issues, it's really no surprise.
3. Dean can't trust Sam
(5x01 "Sympathy for the Devil")
You know, I originally had this moment at number two, but I switched it to number three after writing up the bit about the next one. You see, my opinions are variable. Just like the relationship of Sam and Dean! Hjuck hjuck. Moving on. Though at this point it seemed like Sam and Dean had gotten things back on track after their major break up over killing Lillith via demon blood, it turns out that Dean hasn't forgiven Sam after all. And it's not just that he hasn't forgiven him, because even Sam understands that that will take time, but he doesn't trust him anymore, and that by far is probably one of the worst things for Sam to ever hear. So much of their relationship is being able to depend on each other no matter what, but it was all thrown for a loop when Sam decided to go with Ruby instead of Dean. It's not really repaired until Dean realizes just how much Sam has faith in him way down the line.
As I mentioned above somewhere, while Dean often takes out his frustrations in the form of a punch to the face, it's sometimes his words that are much more painful. Case in point, here. After everything they've been through, Dean has finally decided to just give himself over to Michael and get it over with. Sam tries to get through to him that he shouldn't, but that's when Dean gets to his cutting remarks. His reason for wanting to give in is that he doesn't believe that Sam will be able to resist Lucifer. He's convinced that Sam will eventually say yes, and since he believes that will happen, he has to say yes too. That really broke Sam's heart, more than anything else could, I'm sure. But, he's the bigger man this time around, having faith in Dean when Dean doesn't return the favor (at first). Eventually Dean does come to his senses, but this was a seriously low moment that showed just how broken Dean had really become, and how far their relationship had gone downhill.
1. Big ole fisticuffs
(4x21 "When the Levee Breaks")
I briefly mentioned this moment above when I was talking about Dean not being able to trust Sam anymore, and it's all because of this moment here. Though the boys had been getting in fights throughout the season about Sam's trust in Ruby, it all came to a head when Sam took off with her rather than detox himself from the blood and do things the way Dean thinks they should be done. Dean follows him and they get into probably their worst fight ever, both of them saying many terrible things to each other, and eventually leading to fisticuffs (that's fighting with your fists, you know). Sam gets the better of Dean in the fight and leaves with Ruby, leaving Dean alone and beaten on the floor. Their last words to each other, in the image above, are chilling, and I would say this is probably the lowest point in their relationship, as they are both upset with each other, rather than it being more one-sided, like some of the other moments.
Next week I will be going over the top five episodes of season two.
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