Few characters in TV history have been through as much as Sam Winchester, other than perhaps his older brother. Across 15 seasons of Supernatural, Jared Padalecki’s character carried the enormous emotional weight of balancing his love for his brother Dean, his struggle against destiny, and the constant temptation of darkness, because he’s the poster boy for Hell. Though he was younger, Sam always seemed the more pragmatic and grounded of the two. Though a lot of the episodes showcase the Winchester brothers equally, some stand out as especially Sam-centric, giving fans a deeper look at his complexity.
From the heartbreaking sacrifices to hilarious misadventures, these ten episodes are prime examples of the very best of Sam Winchester.
10) “Time for a Wedding” (Season 7, Episode 8)
Though Dean gets a lot of the goofier episodes (alongside the dark ones), Sam gets a few, so not every Sam episode has to be tragic. In “Time for a Wedding” it’s the younger Winchester’s time to be the butt of the joke. In this hilarious detour, Dean finds Sam rushing to the altar at a Las Vegas wedding chapel, eager to marry Becky, the Supernatural (novels) superfan and Supernatural (TV series) fan-favorite.
In a premise that puts a comedic, Supernatural twist on Stephen King’s Misery, Becky essentially “magic roofies” Sam with a love potion, and when it inevitably wears off, she resorts to tying him up so he can’t escape.
It’s a silly and strangely charming episode that gives us a break from the usual storyline intensity and allows Jared Padalecki to flex his comedic chops. Not only that, but it gives the audience a chance to be reminded of Sam’s empathy and patience, even towards a slightly unhinged superfan with the cringey username “samlicker81.”
9) “After School Special” (Season 4, Episode 13)
The Supernatural flashback episodes are always a welcome watch. Fans love a deeper dive into the formative years of Sam and Dean, and “After School Special” stands as one of the best. This story takes us back to the high school years, where — for possibly the last time — Sam is shorter than Dean.
It’s a great example of how differently the boys existed in the world. While Dean was reveling in being the “new cute guy” in school, Sam was struggling to fit in, juggle school, and learn how to keep what his family does a secret. What’s nice, however, is that Dean is still watching out for his brother, though in a slightly more distant capacity.
The episode captures the poignancy of Sam’s childhood and the influences that likely drove him away from his family when he initially rejected the life of a Hunter. It reminds us that while Dean accepted the life of his father early, Sam always wanted something else. But there’s also the main storyline itself, which gives us a truly heartbreaking look at the personal battles Sam carries with him. His one school friend, Barry, is the vengeful spirit; haunting the halls of the school where he took his own life. When Sam realizes that Barry couldn’t cope at school after the Winchesters blew town, he is wracked with guilt. Dean does his best to comfort his brother, but Sam being Sam, is unable to forgive himself for something he feels he could have prevented.
8) “Just My Imagination” (Season 11, Episode 8)
Another insight into Sam’s childhood comes much later in “Just My Imagination.” When his childhood imaginary friend Sully shows up in the present day, fans are treated to an intimate look at young Sam’s loneliness and need for comfort in a world where monsters lurked around every corner, and he had no true safe space.
It’s an interesting dynamic as an episode. There is some absurd humor that comes along with the brutal, gory deaths of imaginary friends, but it also serves as a heartbreaking moment of realization for Dean that Sam couldn’t — or wouldn’t — tell Dean everything, even as a vulnerable kid. It’s also worth noting that Sam’s matter-of-fact way of admitting why Sully exists, and nonchalantly explaining that he was lonely as a child, shows how much work he has done to accept that. It’s a very mature moment, and shows Sam’s growth.
7) “When the Levee Breaks” (Season 4, Episode 21)
“When the Levee Breaks” is one of the darkest Sam-centric hours of the series. After Sam has spent the entire season chowing down on demon blood, He’s finally caught and locked in Bobby’s panic room to detox. His withdrawal manifests in dark hallucinations that force him to confront his choices and deepest fears.
It’s a brutal and heartbreaking episode, and it’s easy to see why. Watching Sam spiral between rage, desperation, and guilt highlights the cost of his choices, while cementing his complicated relationship with Dean. It’s a gut-wrenching reminder of how far Sam was willing to go in pursuit of saving the world, and how quickly that can be contorted into something sinister.
6) “Our Father, Who Aren’t in Heaven” (Season 15, Episode 8)
But let’s get back to some sweeter moments (albeit brief), and another — this time consensually — coupling up for Sam with Eileen Leahy. In Season 15, Sam and Dean are joined by Eileen, a hunter who first appeared back in Season 11, and had quite the effect on Mr. Winchester. By Season 15, they have a somewhat “unlabeled” relationship, which is definitely more than platonic.
Within the deeply intense final season, where they are at the final boss level, it’s nice for Sam to have something good. It’s interesting to see him care for someone other than his brother, but when Eileen calls him out for worrying, and he sees quite how badass she is, he respectfully backs off.
Their relationship shows how much Sam has grown since the early seasons. For much of Supernatural, he wrestled with control, whether over his powers, his destiny, or even the people he loved. With Eileen, however, we see a different side. It underscores that Sam isn’t just defined by his trauma or his role as Dean’s brother; he’s also capable of building genuine, respectful connections, and feeling safe to show his softer side.
5) “Mystery Spot” (Season 3, Episode 11)
Winding it back to one of the earliest seasons and you can see the contrast between Sam in Season 15 and Sami in Season 3. One of the most iconic Supernatural episodes ever, “Mystery Spot” is Sam’s (and Jared Padalecki’s) personal nightmare. Padalecki has openly admitted it was one of his least favorite to shoot. In a Supernatural homage to Groundhog Day, Sam is forced to relive the same day over and over, and face the trauma of watching Dean die hundreds of times, each one becoming more bizarre and slapstick, but no less real for Sam.
It’s a perfect blend of dark comedy and emotional devastation, with the Trickster’s usual cruel games becoming a sinister gut-punch of grief. It highlights that Sam will never stop trying to save his brother, but also offers one of the earliest glimpses of how terrifyingly focused he can become when left without Dean.
4) “Stranger in a Strange Land” (Season 14, Episode 1)
And that focus (and frankly badassery) is on full display during Season 14. The season’s premiere episode put Sam in the driver’s seat. With Dean’s body possessed by the archangel Michael, Sam calls on a group of hunters to track him down. He even steps into the lion’s den by meeting with the demon Kipling. It’s a rare moment in Supernatural history where Sam gets to navigate situations in the role of leader opposite fellow hunters, rather than standard citizens.
By the writers effectively “hobbling “Dean and putting Sam in uncharted waters, it cemented the proof of Sam’s capacity to move forward without his brother, even when he doesn’t want to. He is feared among demons to the point that they won’t even fight his refusal to allow a new King of Hell, and that’s some pretty impressive fearmongering.
3) “The Man Who Knew Too Much” (Season 6, Episode 22)
Sam’s fractured psyche takes center stage in this Season 6 finale. After Castiel’s betrayal brings down Sam’s protective mental walls, Sam battles through his own mind to discover his soul is split into three versions. He has the soulless Sam, the core Sam, and the tortured soul who remembers Hell. What follows is a psychological showdown as he tries to put the pieces back together.
Jared Padalecki is a tour de force in this show, doing a great job of capturing Sam’s internal struggle in three different physical performances, making “The Man Who Knew Too Much” a standout entry in his long battle with identity and trauma.
2) “All Hell Breaks Loose, Part 1” (Season 2, Episode 21)
If there’s one storyline that cemented Sam Winchester’s importance to Supernatural, it’s the Season 2 finale. When he’s kidnapped by Azazel and discovers other “special children” just like him, Sam takes it upon himself to keep the group together and try to work the problem. But when they learn that it’s all a deadly competition, Sam meets his end at the hands of Jake Talley. Dean’s desperate decision to sell his soul to bring Sam back sets the foundation for the next several seasons.
It is some powerful storytelling and remains one of the most defining chapters of the Winchester saga. This episode not only showcased Sam’s strength and moral compass but also showed us that Sam wasn’t going to be defined by the demonic hand he’d been dealt.
1) “Sacrifice” (Season 8, Episode 23)
The Season 8 finale is one of Sam’s most heroic moments, and another example of him stepping up to take the lead. After a season spent repairing his fractured relationship with Dean, Sam is the one to volunteer and complete the trials to seal Hell forever. Across three episodes within the season, we watch Sam get through the trials, causing excruciating damage after each one. The emotional climax between the brothers, with Dean begging Sam not to go through with it, remains one of the show’s most powerful scenes.
We get one of Sam’s most emotive speeches when he professes that his greatest failure is always letting Dean down. Both actors bring the emotive chops, but Jared Padalecki really hammers the painful nails in.
Which Sam Winchester episode is your favorite? Did it make the list? Let us know in the comments!
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