Supernatural is grounded in the relationship between the Winchester brothers. As individual characters, Sam and Dean engage us, but it’s their relationship as brothers that really draws us in. Sam (Jared Padalecki) and Dean (Jensen Ackles) are shaped by losing their mother as children and being raised as hunters by their father, though each react to these life experiences in different ways. The complex and evolving portrayal of Sam and Dean as brothers has kept us engaged through ten seasons of Supernatural.

In our “Supernatural Starter Guide” we discussed how episodes tend to fall into certain themes: family, scary monsters, heaven and hell, and witty metafiction. Here we explore the Winchesters brothers’ complicated family relationships and how these experiences have shaped them. The following episodes, ordered by release date, provide an enriched understanding of how Sam and Dean relate to each other and how they have been shaped by their life experiences.

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“Pilot” (Season 1, Episode 1)

As children, Sam and Dean lost their mother, Mary (Samantha Smith), in a violent and bizarre manner. Thereafter, their father, John (Jeffrey Dean Morgan), raised them as hunters who track down monsters, demons, and other supernatural creatures (“saving people, hunting things—the family business’). Dean had continued to hunt with his father as an adult, while Sam went to college at Stanford University. When we first meet the Winchester brothers as adults, Dean comes to see Sam at college. Sam has just been accepted to law school and is living with his girlfriend Jessica. Dean convinces Sam that they need to go in search of their missing father. They find their dad’s hunting journal and clues to a case he had been working on in Jericho, California, but no signs of John Winchester.

The pilot of Supernatural successfully introduces a complex backstory, keeps us on the edge of our seats with an exciting storyline, and engages the audience with characters we want to keep watching. The actors had good chemistry and felt like fully formed characters, which is unusual for a pilot. Even if you came to Supernatural late in the series, the pilot is a must-see.

“Shadow” (Season 1, Episode 16)

The brothers arrive in Chicago to investigate several bloody murders. While in town they cross paths with Meg Masters (Nicki Aycox) and suspect that she is connected to the murders. Sam and Dean begin to wonder if events are being orchestrated by the demon that killed their mother. It becomes clear that things are not what they seem, and Sam and Dean find themselves in a complicated situation.

In “Shadow” we first see the Winchesters use uniforms as a disguise, in this case as workers from a security company. Some of the mystery involving the Winchester family is revealed in this episode, giving us a glimpse of things to come. We learn that though family connections often strengthen the Winchesters, it can also be a weakness—a theme that is reiterated in the series. The continuing differences in the brothers’ perspectives on the hunter life become clear when Sam says to Dean, “I’m not gonna live this life forever. Dean, when this is all over, you’re gonna have to let me go my own way.”

“Something Wicked” (Season 1, Episode 18)

Sam and Dean head to Eitchburg, Wisconsin to investigate why children are falling into unexplained comas. In a flashback to Sam and Dean when they were young, we find that their dad dealt with a similar case. During that case Dean endangered Sam by leaving him alone, despite his father’s instructions. In the present, Sam and Dean struggle with resolving their current case without putting another innocent at risk.

This is one of the first flashbacks to the Winchester brothers’ childhood. Supernatural uses flashbacks very effectively to convey a great deal of information about who Sam and Dean are today. Without these flashbacks, it would be hard for the viewer to understand that their lives as children were similar to their lives as adults—moving place to place, staying in motels, being on their own most of the time, and living with the knowledge that monsters are real. One of the themes of the first few seasons of Supernatural is Sam’s resentment towards his father for raising them in the hunter life. While Dean seems to embrace being a hunter, emphasizing their role in helping people and characterizing their dad as a hero, Sam yearns for a “normal” life. “Something Wicked” shows that Dean has had to give up a lot as well, not only in trying to live up to his dad’s expectations, but also because he has spent most of his life taking care of Sam. This is another important reoccurring theme in the Supernatural series.

“In My Time of Dying” (Season 2, Episode 1)

At the end of Season 1, the boys and their father end up in the hospital. As Dean struggles between life and death, Sam and his father continue to clash. Sam does everything he can to save his brother, but becomes suspicious of his father’s intentions after a visit with Uncle Bobby (Jim Beaver).

“In My Time of Dying” is a very emotional episode. We begin to see just how far the Winchesters will go to save each other. The family conflicts between Sam and his father come to the surface, but are never truly resolved. In a very moving scene, John acknowledges the responsibility he has placed on Dean, saying, “I put too much on your shoulders. I made you grow up too fast. You took care of Sammy, you took care of me. You did that, and you didn’t complain, not once. I just want you to know that I am so proud of you.” The perceptions Sam and Dean have of their life experiences and familial relationships clearly shape who they are in very different ways. “In My Time of Dying” effectively exposes the underlying issues that motivate John, Sam, and Dean and does a great job of setting up the rest of Season 2.

“What Is and What Should Never Be” (Season 2, Episode 20)

We begin ”What Is and Shall Never Be” with the boys on the trail of a djinn. Dean unexpectedly finds himself in a very different world, one in which his mother was never killed and he and Sam were not brought up as hunters. Dean keeps seeing a mysterious woman appear, making him question his reality. Everyone’s life is very different, mostly in good ways, but negatively in terms of the brothers’ relationship and all the people they never saved.

This is a very strong episode in terms of storyline, dialogue, acting, and scary monsters. As a viewer, you can really feel the bittersweet experience of seeing what could have been for the Winchester family. We are reminded of how much the Winchesters have given up when Dean asks, “Why is it my job to save these people? Why do I have to be some kind of hero? What about us, huh? What, Mom’s not supposed to live her life? Sammy’s not supposed to get married? Why do we have to sacrifice everything, Dad?” Despite what the Winchesters have lost, it becomes evident the brothers wouldn’t have become so close if they hadn’t been so through so much together.

“A Very Supernatural Christmas” (Season 3, Episode 8)

The boys head to Ypsilanti, Michigan to investigate a killer Santa Claus. After realizing that the victims all had wreaths made of a particular herb, the brothers track down the makers of the wreaths. Throughout the episode Sam and Dean have a conflict about celebrating Christmas. Dean’s impending fate has inspired him to want to observe the holiday one last time, while Sam reacts very differently. Flashbacks to Sam and Dean’s childhood show the brothers waiting for their father alone in a motel room on Christmas Eve. Dean is conflicted about keeping Sam innocent about the monster-filled world they live in after Sam finds his father’s hunting journal.

Why can’t Supernatural do a Christmas episode every year like the Doctor Who Christmas Specials? How fun would that be? The wreath-makers, Edward (Spencer Garrett) and Madge (Merrilyn Gann), are very well-crafted characters played by skilled actors. The monster storyline is really well done—scary, suspenseful, funny, and clever. If the episode had just been a standalone Monster of the Week episode it would have been quite good, but the writers did an impressive job of taking us deep by including the brother’s storyline. We again see the theme of Dean taking care of Sam, but in a way that demonstrates that they boys are always there for each other. “A Very Supernatural Christmas” is also the first time we learn where Dean’s “Samulet” comes from, becomes a significant icon in later episodes.

“No Rest of for the Wicked” (Season 3, Episode 16)

The Winchesters are desperate to save Dean as the end of his contract is coming close. With Bobby’s help, they head to New Harmony, Indiana, where the demon Lilith (Sierra McCormick) has possessed a little girl and is essentially holding the family hostage. They decide that the only way to save Dean is to go after Lilith. The demon Ruby (Katie Cassidy) claims she wants to help them, but Dean remains unwilling to trust her.

“No Rest for the Wicked” is straight-up terrifying. Lilith in the form of a little girl is frightening, disturbing, and comical all at the same time. There are two classic scenes in this episode, both of which connect to the theme of family. The first is when Bobby says to Dean, “Do I look like a ditchable prom date? … Family don’t end with blood, boy!” The second is when Sam and Dean are in the Impala on the way to attack Lilith. Sam wants to talk, but Dean refuses, saying, “No, you’re not gonna bust out the misty goodbye speech, okay? And if this is my last day on earth, I do not want it to be socially awkward,” resulting in them singing Bon Jovi’s “Wanted Dead or Alive.” The last ten minutes of the episode are thrilling and bring Season 4 to a very scary and moving close.

“Afterschool Special” (Season 4, Episode 13)

A school haunting takes them to a high school they had attended for a short time. Dean goes undercover as a gym class teacher (a disguise beloved in Supernatural cosplay), while Sam infiltrates the school as a janitor. In a series of flashbacks, we find that Sam and Dean had very dissimilar experiences at school. Young Dean (Brock Kelly) arrives at school all cool and casual, while young Sam (Colin Ford) is picked on by a bully. Dean can’t understand why Sam doesn’t use his hunter skills to just take care of the bully, but Sam just wants to be a normal kid at school.

It’s compelling to watch Sam and Dean placed among other kids their age in a school. This is the definitely the spin-off CW is looking for—sort of a Supernatural Smallville. The flashbacks provide us an interesting glimpse into the way their transient lives as hunters affect the young Winchesters. At the start of the episode, Sam is begrudgingly resigned to become a hunter when he grows up, while Dean glorifies the independence that comes with his father being gone hunting all the time. By the end, Sam begins to realize he has other options, while Dean sees his life though another person’s eyes and realizes his life may not be as glamorous as he likes to imagine.

“When the Levee Breaks” (Season 4, Episode 21)

When it becomes apparent that Sam has been making some very questionable choices, Dean and Bobby lock him up at Bobby’s panic room. As Sam hallucinates, Bobby questions if they are doing the right thing. He points out that perhaps Sam’s plan is the only way to prevent the Apocalypse, but Dean is not willing to sacrifice Sam. In search of help, Dean goes to Castiel (Misha Collins), who will only help if Dean promises to serve Heaven. The conflict between Sam and Dean comes to a head at the end of the episode, with one of the most intense scenes between the brothers in the series.

Sam is determined to save his brother from being a monster, while Sam is convinced that only he can stop the Apocalypse. “When the Levee Breaks” highlights a theme regarding Sam’s nature that has run through the entire series. It explores whether Sam’s experiences with demons are destined to make him a hero or a monster, as well as the continuing question of whether Dean will need to save Sam and what will happen if he cannot. This episode is fraught with emotion. Sam’s hallucinations show us how he perceives his place in the coming Armageddon and within his own family, while Dean’s conversations with Bobby reflect the continuing responsibility he feels for Sam.

“Dark Side of the Moon” (Season 5, Episode 16)

The first scene of “Dark Side of the Moon” may be the best cold open in the entire series. It is a shocking scene that is only enhanced by Jensen Ackles’ skill at appearing terrifying in the face of imminent danger. Castiel encourages the boys to get more information about God’s wishes while they are “behind enemy lines.” As Sam and Dean revisit past scenes from their lives, it becomes evident that they saw their lives growing up very differently. While Dean recalls time spent with his brother and mother, Sam remembers times he was on his own.

A theme of Season 5 has been how Sam and Dean’s relationship to their father mirrors that of Michael and Lucifer. The parallel between these sets of brothers was first directly voiced by Gabriel in “Changing Channels” (S05E08). Dean/Michael represents the good son that does his father’s bidding, while Sam/Lucifer rebels against a father perceived as absent and unfair. “Dark Side of the Moon” reflects this idea, but provides greater context about how the differences in their life experiences have shaped their individual views about family. Dean’s caretaker role reinforced his commitment to hold the family together, while Sam constantly craved a stability he never had a chance to experience. “Dark Side of the Moon” is referenced in the 200th episode, “Fan Fiction” (S10E05), specifically when Dean threw away the “Samulet” after losing faith both in God and his brother.

“Swan Song” (Season 5, Episode 22)

“Swan Song” is narrated by the prophet Chuck Shurley (Rob Benedict). Chuck describes how the Impala has served as a home for the Winchesters over the years. Despite his own fears of losing his brother, Dean has resigned himself to Sam’s decision to say yes to Lucifer. The brothers hope that Sam will be able to trap Lucifer with the Four Horsemen’s rings. Things don’t go as planned as Lucifer is one step ahead of the Winchesters, and the final battle between Lucifer and Michael appears imminent.

“Swan Song” is the culminating episode in what creator Eric Kripke originally envisioned as a five-season series. It is still often referred to as one of the best Supernatural episodes and it’s probably our favorite (it’s so hard to choose!). “Swan Song” also makes our list for the top “Angels and Demons” episodes. It is only because of the connections that Sam and Dean have with each other that they even have a snowball’s chance in Hell against Lucifer. Their powerful connection was forged through both good and bad times, during which they learned to rely on each other. As Chuck tells us in the narration, “Up against good, evil, angels, devils, destiny, and God himself, they made their own choice. They chose family. And well … isn’t that kinda the whole point?” “Swan Song” is also known for leaving viewers wondering just who Chuck really is.

“We Need to Talk about Kevin” (Season 8, Episode 1)

After being trapped for a year, Dean manages to escape with the help of vampire Benny (Ty Olsson). Dean reconnects with Sam in Whitefish, Montana, but becomes angry when he learns Sam hasn’t been searching for him. Instead, Sam has given up hunting and is living a “normal” life. In the meantime, prophet Kevin Tran (Osric Chau) has been in need of Sam’s help.

Dean and Sam have always had a deal that the other should move on and live his life if one of them dies, but this is the first time one of them has actually done so. Though Dean did live a civilian life with Lisa for a year when he thought he lost Sam, he still did everything he could to try to get Sam back. Despite Sam’s explanation that he had no idea what had happened to Dean or where to look for him, Dean is angry. Sam had often expressed a desire to live a “normal” life in their early years of hunting, and was able to do so for a time. When Dean returns, they return to hunting, despite the tension in their relationship.

“Bad Boys” (Season 9, Episode 7)


Dean and Sam head to a reform home for boys in Hurleyville, New York, when a man has been mysteriously killed. The boys home is headed by Sonny (Blake Gibbons), who Dean became close to when he spent two months there when he was a teen. In flashbacks we learn that young Dean (Dylan Everett) did well at the home and in school, and developed a romance with a girl, Robin (Sarah Desjardin). When he returns to the area he runs into Robin (Erin Karpluk) again.

This whole chapter of Dean’s life was a revelation to Sam. It’s evident to the viewer that Dean sacrificed the possibility of a somewhat normal teen life to stay with his family, particularly Sam. Though Dean does not share any of this with Sam, it gradually becomes clear to Sam that Dean gave something up when he left the home. Until this episode, we hadn’t seen much around the theme of the Winchesters’ lost childhood since Season 5. “Bad Boys” has some similarities to “A Very Supernatural Christmas” and “Something Wicked” in terms of Dean feeling responsible for Sam. Yet the flashbacks to Dean’s childhood in “Bad Boys” show us Dean on his own, thriving. It’s a very moving episode that fits well in Season 9, when Dean is desperate to not lose his brother. While Dean may feel responsible for Sam, he also loves his brother and will always choose family.

“Do You Believe in Miracles” (Season 9, Episode 23)


Dean seems to have lost control because of the Mark of Cain, so Sam and Castiel lock him up in the bunker. Gadreel (Tahmoh Penikett) reveals that Metatron (Curtis Armstrong) wants to take the place of God, using the power of the angel tablet. Sam goes after Metatron on his own, while Castiel and Gadreel decide to go after the tablet in Heaven. Dean enlists the help of Crowley. Complications ensue, resulting in a heartbreaking and shocking end to the season.

Though the plot is a bit convoluted, Sam and Dean have some very emotional scenes together in the second half of the episode. Jared Padalecki and Jensen Ackles are quite a remarkable acting team. Their characters play off each other so well that they improve each other’s performances by virtue of being in the same scene. No matter how many times something terrible happens to one of these characters, we are still completely drawn in. Because each actor is able to so expressively convey the loss of the other, we feel it too.

“Soul Survivor” (Season 10, Episode 3)

In “Soul Survivor,” Sam has captured Demon Dean and is holding him in the bunker. Sam has procured sanctified human blood as a demon cure in order to turn Dean back into a human. Dean taunts Sam about being a monster for the things he has done to find his brother. Sam grapples with the fear that he may have to kill Dean if he cannot cure him. Sam reminisces, looking at family pictures of Bobby, Dean, and their parents. As things go awry, it becomes unclear if Sam is going be able to save Dean after all.

“Soul Survivor” shows us what lengths Sam will go to in order to save his brother. Traditionally Dean plays this role, whereas Sam has sometimes embraced the idea of moving on, one way or another. In Season 10 we see that Sam is willing to go to extreme lengths to save his brother.

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What’s Your Favorite?

Supernatural does a great job of making us feel connected to the lives of the Winchesters. Providing an emotional backdrop to the scary monsters we see each week keeps us coming back for more. As for the Supernatural episodes focusing on the Winchester brothers’ relationships, which are your favorites?