Sam and Dean Winchester’s Most Hilarious and Heartbreaking Brotherly Moments From ‘Supernatural’

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Many fans have been mourning the conclusion of the 15-year run of Supernatural. One thing that has kept fans around for the show’s duration is its idea of family, especially the aspect of Dean’s and Sam’s brotherly bond. Over the years, the pair have shown their dedication to one another and sacrificed a considerable amount in their lives to keep the world a safer place. In an effort to keep Supernatural’s memory alive and kicking, we’ve compiled some of our favorite brotherly moments to put you in your feels. Unfortunately, it seems as though some of our favorite moments may also be the most distressing — so grab those tissues, folks. Don’t worry, we added some comic relief to help you laugh through the tears.

Season 2, Episode 21 & 22: “All Hell Breaks Loose: Part 1 & 2”

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There are a few scenes worth mentioning in these last two episodes of season 2. As fans may remember, Sam dies (and stays dead for some time) after being stabbed in the back by Jake, who was among Sam and others in a ghost town organized by Azazel. Dean tries to warn Sam, but it’s too late. Dean clinging to Sam’s nearly lifeless body as Sam slowly loses consciousness is a heartbreaking brother moment we wish we didn’t have to see; Dean calling “Sam”, as tears stream down his face makes the audience grieve alongside him. Also worth mentioning is the scene where Dean talks to Sam’s body on the bed. As a viewer, this was one of those rare moments of vulnerability for Dean. He is broken, talking to his little brother, whom he feels he has failed. Once Dean makes a deal and returns back to Sam, their embrace warms the audience’s hearts as the brothers’ hunt for Azazel continued.

Season 4, Episode 10: “Heaven and Hell”

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Remember when we said to grab the tissues? In the last few minutes of this episode, Dean and Sam are drinking beers on the hood of Baby. Dean says that he knows Sam heard what Alastair said about Hell and how Dean showed “promise.” Sam assures his brother that while he did hear, he isn’t pushing him to open up. Dean pauses and then explains to Sam how he experienced 40 years of Hell. As he explains, he becomes so overwhelmed with emotions — guilt, shame, and anger — that he breaks down into tears. He discloses to Sam how they tortured him, and how everyday Alastair gave Dean the option to get off the rack in exchange for another soul to take his place. For 30 years, Dean told Alastair to “stick it where the sun shines.” As he continues and Sam looks visibly shaken from Dean’s harrowing testimony, Dean tells Sam that he took Alastair up on his offer and “started ripping them apart.” It’s not often that we see Dean lay out all his emotions, especially in front of his little brother Sammy, but Dean knew that if he held this in any longer, it would destroy him. Sam, while wiping his own tears away after imagining what his brother must’ve gone through, tries to comfort Dean by saying that he held out as long as he could. In one of the last lines in the scene, Dean states,

I wish I couldn’t feel anything, Sammy. I wish I couldn’t feel a damn thing.

This scene sticks with many fans, not only for its difficult subject matter, but for the performance of Jensen Ackles and Jared Padalecki. No matter the circumstance, the brothers are always there for each other.

Season 5, Episode 22: “Swan Song” 

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We will always remember that fateful day at Stull Cemetery. In one of the most powerful moments of the entire series, the Winchesters’ brotherly bond played a major part in what at the time was unthinkable — averting the Apocalypse and saving the world. After Sam had accepted Lucifer in an unsuccessful attempt to end his impending reign of terror, Dean — in true reckless (badass) fashion — drives his car right into Stull Cemetery, interrupting the final showdown in a last-ditch attempt to save his brother. While he quickly realizes that neither of them might be making it out of the situation alive, the ever-loyal older sibling stays with his brother to face the end. As Lucifer is frankly beating the crap out of Dean, the glint of the beloved Impala, the boys’ true home, catches his eye, triggering a barrage of Sam’s most treasured brotherly memories. This gives Sam the strength to briefly take control, gather his nerve, say goodbye to his brother, and fall into the pit.

It’s okay, Dean. It’s gonna be okay. I’ve got him.

While heartbreaking, this important moment perfectly showcases the irrevocable bond between the Winchester brothers, something that will prove time and time again strong enough to save themselves, save each other, and help save the world. 

Season 8, Episode 23: “Sacrifice” 

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In yet another heart-wrenching scene, Sam bares his soul and shows his grief to Dean in an attempt to explain why it’s so important to him to finish completing the trials that will close the Gates of Hell. After Sam failed to search for Dean after he and Cas get sucked into Purgatory, things were … strained between the brothers, to say the least. Sam had internalized the guilt and shame that he felt for abandoning not only his brother but “the life” in general, plagued by the reality that he likely could have helped a lot of people that needed him during his hunting hiatus. This guilt was the driving force to finish the trials — Sam wanted to not only pay his penance for abandoning people in their times of need but earn his brother’s respect and forgiveness once more.

You want to know what I confessed in there? What my greatest sin was? It was how many times I let you down. I can’t do that again.

Sam’s angst is palpable, but Dean quickly puts a stop to the notion that their brotherly bond is severed. In one of the most iconic lines of the series, Dean iterates (in that indirect yet direct, roundabout way of his) that he cares about Sam more than the arguments they’ve had, more than the crap they’ve done to each other, more than revenge. This moment is one of many that highlights the strength and resilience of the Winchesters’ bond.

Don’t you dare think that there is anything, past or present, that I would put in front of you!

Season 12, Episode 22: “Who We Are”

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After Sam’s rousing speech rallying the remaining American hunters to storm the British Men of Letters compound, Sam and Dean part ways on their own respective missions — Sam to save the hunters and Dean to save Mary. This is one of the rare times the brothers seem to be operating as two separate units, and the circumstances are especially dangerous with the price on their heads. In a meaningful moment before they part, Dean quietly expresses his pride at Sam’s development into such a capable leader. The two share a rare, non-world-ending hug (wow) and exchange some customary words before setting off on their respective missions including “you come back” and the infamous “Bitch” “Jerk” combo. This scene manages to showcase the quiet rapport that the brothers have built over their lives, with so much feeling infused in a scene with so few words. While imminent danger is still looming for the hunters, this scene doesn’t feel like a goodbye, but rather an “I believe in us” moment as the brothers leave each other to take care of business like they know they can.

Season 14, Episode 12: “Prophet and Loss” 

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Speaking of “I believe in us” moments … Sam’s tearful confession in “Prophet and Loss” was a tough one to watch, not because of the message his words conveyed, but because of the raw emotion behind it. While the Winchesters are no strangers to death and self-sacrifice, Sam is pushed over the edge by Dean’s nonchalance concerning his impending plan to lock himself in the Ma’lak Box. In a torrent of emotion, Sam picks a fight. The younger Winchester unleashes his fury, desperation, and despair on his brother in a long speech asking why, after all they’ve been through, Dean is resigning himself to die.

I believe in us Dean. Why don’t you believe in us, too?

Sam’s obvious anguish convinces Dean to keep looking for more solutions to subdue Michael until they have no other options but to put him in the box. One has to wonder if Dean’s short speech about being able to let go when it was timed was foreshadowing, as the show’s upcoming end was announced not long after this episode aired.

Some Laughter to Dry Your Tears

Season 1, Episode 1: “Pilot” 

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We couldn’t make this listicle and not mention the episode that started it all. Yes, the pilot episode has several moments worth discussing, as well as many celebrated quotes Supernatural fans can recite on command. First, we have to mention Dean surprising Sam in the middle of the night. The struggle, the banter, it’s a classic episode that lives in the hearts of the SPN Family. Once on the road, their back and forth as brothers who haven’t seen each other in several years is comical. For example, when Sam questions Dean’s musical playlist, it inspired the line,

House rules, Sammy. Driver picks the music, shotgun shuts his cake hole.

Other noteworthy moments are when Dean and Sam are running from possessed Baby and after reaching the motel room, Sam informs Dean that he “smells like a toilet.” Towards the end of the episode, Sam drives Baby into “The Woman in White’s” house and once Dean makes sure Sam is unharmed, he says he will kill Sam if Baby was badly damaged. All in all, the episode is a classic reminder to loyal fans of the brother’s history and how their 15-year journey began.

Season 2, Episode 15: “Tall Tales”

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On a less depressing note, there have been quite a few moments where Sam and Dean acted like typical siblings — you know, without all the doom and gloom. Some of the most notable incidents occur in “Tall Tales.” Sam and Dean pull quite a few pranks on one another throughout this episode, reigniting a long-standing prank war that gets increasingly more serious as time goes on. Additionally, as a result of the Trickster’s influence, the boys find themselves getting into multiple petty disagreements, bringing out the sibling in them. It all comes to a head when Sam and Dean start fighting/wrestling like literal children after a disagreement. With all of the heavy moments the show brings, it’s nice to see the brothers act like … well, typical brothers.

Season 3, Episode 11: “Mystery Spot”

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“Rise and shine, Sammy.” Oh, yes. “Mystery Spot” is another fan-favorite episode with some noteworthy brother moments. If you’ll remember, Sam and Dean are stuck in a loop (where only Sam remembers the day repeating itself) and the day ends with Dean’s death. Although it pains us to see Dean die so many times (in increasingly funny ways, though), it’s hilarious to see Sam start to unravel as “Heat of the Moment” by Asia continues to play. On the 100th Tuesday, Sam and Dean are sitting at breakfast and Sam tells Dean he knows everything that’s going to happen. Dean doesn’t believe him. Sam proves it by copying every next phrase or sentence Dean says.

Right, you’re a mindreader. Cut it out, Sam. Sam!

It’s a beloved episode shared by many and it’s another example of our favorite brotherly duo. We can’t imagine living through 100 Tuesdays, and we sympathize with Sam for being so grumpy.

Season 8, Episode 20: “Pac-Man Fever”

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Back in Season 8, Sam’s body is worn down from completing two of the three trials from the Demon Tablet. At the beginning of the episode, Sam appears from a 12-hour “siesta” and Dean throws a beer to Sam. To Dean’s surprise, Sam misses. Dean without missing a beat states, “That’s why we can’t have nice things, Sam.” Additionally in the same scene, Dean tells Sam as he walks closer that he just needs “five minutes with some clippers,” referring to Sam’s long hair. Sam chimes in and tells him to “shut up.” This scene helps show the audience that Dean and Sam, amongst all the lack of normalcy in their lives, they can still find time to have these jokingly brother moments. While it’s a short scene, it’s a notable brother moment we can’t help but watch again with laughter.

While these moments may be mostly sad in nature, they showcase the Winchesters’ ability to support each other, even as the world was crumbling down around them. Sam and Dean’s loyalty to one another persevered time and time again, something that ultimately allowed them to help save the world — on more than one occasion. These moments throughout the entirety of the series continually reaffirmed their fraternal bond, allowing for the continuation of one of the show’s most important legacies, the theme of family, and for that, we will be eternally grateful.

Authors: Kailey, Kenedi

Kailey

Written by

Kailey has been a writer for Nerds and Beyond since 2018. She received her bachelors degree in Communication Sciences and Disorders in May of 2020. Some of her favorite TV shows are The Blacklist, Supernatural, and Prodigal Son, to name a few. She also loves all things Disney! You can check her out on social media @kaileygross.

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