Supernatural: 15 best Sam Winchester moments, ranked

Louis Skye

What are the best Sam Winchester moments on Supernatural?

Sam Winchester, little brother, researcher, hunter, sass-master, a sacrificial lamb, and an all-around great character, has made The CW’s Supernatural one of the more memorable shows on TV.

But what makes Sam Winchester (Jared Padalecki) stand out from the plethora of characters gracing our screens in the 21^st century? One could say it’s his selflessness, his love for his big brother Dean (Jensen Ackles), the fact that he’s ready to fight even when the chips are down.

Sam is all that and more—he’s the Winchester with the biggest heart and the most to lose because he’s lost everything multiple times. But it’s Sam’s indomitable spirit that makes him so special to fans.

15. Sam Winchester Saves the Day… and Dies

Remember in the early seasons of Supernatural when the scariest thing to happen was Sam being one of Azazel’s ‘psychic children’? Innocent times!

But the psychic children arc gave us one of Sam Winchester’s most heroic moments—and shone a light on his personality.

As fans, we have become less trusting of the people around the Winchesters, but back in Season 2’s two-part finale, ‘All Hell Breaks Loose’, Sam was still more trusting. He hoped to save himself and the rest of the psychic children from Azazel.

And he almost succeeded—with only Jake Talley (Aldis Hodge) left of the children, Sam was almost home and dry. Talley’s sudden attack on Sam could have been the end of things but Sam continued fighting—knowing that Bobby Singer (Jim Beaver), and his brother Dean, (Jensen Ackles), may not be able to come and save him.

Overpowering the super-strong Talley took everything of Sam, but he succeeded—only to be stabbed in the back, literally, and died in his brother’s arms.

This would mark the first of many times that Sam and Dean died on Supernatural, but it was a shocking moment—and led to Dean’s major sacrifice to save Sam’s life.

14. Sam Winchester Has a Bad Day

Dean Winchester is widely known as the wiseass of the brothers, but Sam has had his moments of sass and humor that stand out. His drunken ‘rant’ at Dean in Season 2’s ‘Playthings’—where he maturely called his brother “bossy… and short”—was close to making this list but we have to go with a classic that still lives with fans.

I am, of course, talking about the iconic Sam Winchester line, “I lost my shoe”, from Season 3’s ‘Bad Day at Black Rock’.

A fan-favorite episode because of the number of laughs it produced, none is more memorable than Sam’s plaintive missive about his lost accessory.

The story revolves around a cursed object, a Rabbit’s Foot, that grants the holder incredible amounts of luck. But it’s also incredibly easy to lose hold of the foot, and that’s when all the bad luck comes crashing down.

When Sam has the Rabbit’s Foot, he’s riding a crazy wave of good fortune that goes bad super-fast once the item is stolen by Bela Talbot (Lauren Cohan).

Sam’s bad fortune includes spilling hot coffee on himself, knocking over waiters with trays of food, skinning his knees, and stepping on chewing gum.

It is the latter incident that leads to everyone’s favorite moment—Sam tries to get the gum off by scraping his shoe against a grate, only for the shoe to fall down the grate. Sam looks so despondent when he announces to his brother that he has lost his shoe, but it is a moment that never fails to evoke uproarious laughter from fans.

What’s worse, Sam proceeds to get captured and almost killed soon after, which is equally hilarious. Luckily his big brother is around to save him.

13. Sam Saves Dean in ‘Mystery Spot’

From the ridiculous to the equally ridiculous, and then to the sublime. Season 3’s ‘Mystery Spot’ is beloved by fans and makes its appearance in many a favorite Supernatural episode list.

The plot is nothing short of hilarious—if a bit macabre. When Sam and Dean head to a place touted for not obeying the laws of physics, Sam finds himself stuck in a time loop. The same Tuesday repeats endlessly, resetting every time Dean is killed, in more and more outrageous ways.

This is a riot of an episode but as it progresses, with Sam becoming increasingly frustrated at not being able to save his brother, one gets the sense that seeing his last living relative die in multiple ways is beginning to play on Sam’s mind.

One would think that solving the mystery would bring the episode to a satisfactory end—but this is Supernatural. When Sam discovers that the Trickster (Richard Speight Jr.) is behind the time loop, he manages to end the loop and usher in Wednesday. Only for Dean to be killed—permanently, this time.

Sam owns this episode, but it is in this last act—spanning about six months—where he really comes into his own. Determined to save his brother by any means, Sam becomes the kind of dogged hunter he never wanted to be. Until he finally has what he needs to trap the Trickster and bring back his brother.

The tonal shift in the episode can be jarring but as a vehicle to show how much Sam loves his brother, few plotlines can rival ‘Mystery Spot’.

12. Samifer! Aka, Sam as Lucifer

This isn’t a ‘great’ Sam Winchester moment, because technically, Sam being possessed by Lucifer—the amalgamation is affectionately known as Samifer—is all kinds of bad and terrible.

Having said that, one of the most enduring scenes in Supernatural history belongs to Samifer in Season 5’s incredibly entertaining—and prescient—‘The End’.

In the episode, Dean is sent into the future to learn what will happen if he doesn’t become the vessel of Archangel Michael. Dean meets his future self—who is very jaded and disgruntled—a hippie version of Castiel, and Chuck Shurley (Rob Benedict), who correctly predicts 2020’s run on toilet paper.

But the most eerie—and aesthetically stunning—moment comes when Dean finds his older self murdered at the hands of Samifer. Forget the devil horns and tail—Samifer is outfitted in a dazzlingly bright white suit, speaks in a clipped, elegant tone, and is surprisingly reasonable.

One could argue that ‘The End’ is a shining example of Padalecki’s chameleon-like acting as Sam Winchester—but there’s definitely a bit of Sam in this version of Lucifer.

When Lucifer possessed Nick, he didn’t embody this suave, James Bond-esque creature—that’s all Sam.

And the Supernatural team clearly know how much fans love Samifer. There’s a brilliant throwback to this scene in Season 15—complete with Samifer in the white suit—that has us on tenterhooks about how the show will end.

11. Lucifer is No Match for Sam Winchester

The Season 5 finale, ‘Swan Song’, was set up as a possible series finale—but 10 years on, we know that the episode ushered in so many plot elements that have become synonymous with Supernatural, and Sam Winchester’s destiny.

For the five-season run-up to this episode, Sam Winchester had been through numerous losses—he’d watched his girlfriend die at the hands of a demon, he’d seen his father sacrifice himself for Dean, he’d seen Dean make a deal with a demon to save Sam. The demon Ruby (Genevieve Padalecki) had convinced Sam to drink demon blood to get stronger—and then proceeded to betray him.

But worst of all was Sam finding out that he was destined to be the human vessel for Lucifer, while Dean was meant to be the Archangel Michael’s vessel. As fates go, this was a rough one—having to embody the very evil that one’s family has been fighting their entire lives isn’t an ideal destiny for anyone.

For Sam, the situation was made worse by the fact that he had little choice in the matter—to ensure the future was set right, he had to sacrifice himself to Lucifer’s mercies. And no human, once possessed by a demon, could possibly get back control, could they?

Sam Winchester is no ordinary human. He fought back against Lucifer long enough to save the day—even though it meant leaping into the Cage that had locked Lucifer in for eons. A fate worse than death but Sam Winchester was ready to make the sacrifice play to save the world.

10. Soulless Sam Tries to Be Human

Granted, Soulless Sam doesn’t exemplify the best that Sam Winchester could be. One could say that the soulless version of the character is one of the worst things to happen to the Winchesters.

But the Winchester’s loss is a big win for us fans because Soulless Sam is one of the most entertaining iterations of a character to grace Supernatural.

The brilliance of Soulless Sam is exemplified in Season 6’s ‘Clap Your Hands if You Believe’, where Sam and Dean investigate a town known for its alien abductions.

Having recently discovered that the reason why Sam had been acting strange since returning from hell was because his soul was still in the Cage with Lucifer, Dean tried to teach his soulless brother empathy. Easier said than done—imagine trying to teach empathy to someone who can’t even grasp the concept.

However, Soulless Sam does his best to be empathetic—and by best, we mean the absolute bare minimum. Sam antagonizes everyone in the town with his blunt interrogations, abandons Dean during a supposed alien abduction, and gets together with an attractive UFO-enthusiast, mere hours after Dean’s abduction.

And he doesn’t really feel that sorry for any of it—Soulless Sam comes to the conclusion that having a soul means endless suffering, so he’s happy the way he is. Leading to more entertainment for us fans.

The reason why the Soulless Sam arc works so well is because Padalecki comes into his own when he’s playing this version of the character. His reactions are genuine and cold—he’s a sociopath in the skin of the protagonist we all love. Yes, he does some horrible things, but he has a ton of fun doing it!

9. Sam Winchester Can’t Act

Season 6’s ‘The French Mistake’ has many detractors among Supernatural fans, but I still stand by this meta episode that was a laugh riot, while advancing the plot for the season.

With Sam and Dean in danger from the Archangels, Castiel (Misha Collins) sends the brothers into an alternate dimension without magic. It just happens to be the ‘real world’, where Sam and Dean are mistaken for their real actor selves—Jared Padalecki and Jensen Ackles.

The brothers have to take the place of the actors—though it involves wearing make-up, putting up with the ‘real Misha Collins’, and even acting.

Sam Winchester may be a great scholar and hunter, but he is a dreadful actor. The brothers manage to avoid doing any real acting for most of their time in the alternate universe. Instead, they spend all their counterparts’ money on magical objects they hope will help them win the war against the angels.

But eventually, they are dragged onto the set and made to act—and unlike the real Padalecki and Ackles, who are expressive and relatable, Sam and Dean are a disaster.

There will never be a greater Supernatural scene than Padalecki and Ackles playing Sam and Dean, pretending to be Padalecki and Ackles playing Sam and Dean very badly. ‘If there’s a key, there must also be a lock’ frequently gets stuck in my head causing me to chuckle to myself in the most inappropriate situations. I’m sure you know the feeling.

8. Sam Lets Lucifer Run his Head

Following half a season of Soulless Sam, the latter half of Season 6 of Supernatural saw Sam finally get his soul back from hell—with dreadful consequences.

Initially protected by a magical mental shield, Sam opts to go through a journey in his mind to restore his Soulless and hell-memories. Despite several obstacles in the way that signals to Sam and the audience, that the destination may not be to Sam’s liking, Sam perseveres.

Ever the sacrificial lamb, Sam takes on the burdens of having a complete soul—Lucifer’s torture and life in hell included. The decision was the right one to make—a world with a soulless Sam Winchester was poorly served.

But a year and a half of torture at Lucifer’s hands had taken a toll on Sam’s mind—as long as he didn’t push himself, he could keep the memories of hell at bay. But once the dam broke, that was the end of it.

Not only was Sam tormented by what he suffered in hell, but he began to hallucinate Lucifer during his every waking moment.

As awful as that sounds, Mark Pellegrino’s faux-Lucifer was nothing short of sassy and hilarious—leading to a major fan-following for his Lucifer. Only Supernatural could make legions of fans adore Lucifer—at least until The CW’s Lucifer came along.

Season 7 of the show was a testament to how much Sam was willing to endure to be a more complete—and safer—human to his loved ones. We wouldn’t expect anything less from him.

7. Sam Winchester Versus the Clowns

It was established early on in Supernatural that Sam Winchester suffered from a case of coulrophobia—a fear of clowns. And who can blame him—clowns are terrifying and not at all funny. The ones in Supernatural are the living embodiment of every person’s nightmare.

So, of course, poor Sam had to confront this fear during Season 7’s ‘Plucky Pennywhistle’s Magical Menagerie’.

Sam and Dean head to a town to investigate a series of magical deaths—unfortunately for Sam, the bulk of the investigations take place in the not-so-happy children’s restaurant Plucky Pennywhistle’s Magical Menagerie, which is infested with clowns.

Being the brave soul that he is, Sam tries to control his fear around the clowns—but then the very thing he fears become the creature he has to fight.

Sam manages to overcome the terrifying clowns and even declares himself phobia-free—or not so much. When Dean hands him a clown toy, Sam dumps it in the street and rides off in the Impala. We would have done the same, Sam.

6. Only Sam Winchester Can Perform a Reverse Exorcism

Demons are part and parcel of Supernatural—granted, they’ve taken a back seat since Season 1, when they were the chief villains.

Sam and Dean Winchester have since been possessed—or in Dean’s case, become a demon. They befriended the King of Hell, Crowley (Mark Sheppard), and they are now co-parenting—alongside Castiel—Lucifer’s son, Jack Kline (Alexander Calvert).

But when demons were still the enemy, Sam showed a true gift for discovering new ways to defeat them—the reverse exorcism.

The Winchester brothers have always had one problem when dealing with demons—the moment demons felt threatened, they would exit the body they were possessing, disappearing into another person or back to hell. Not ideal when you want to question the demon or kill it!

In Season 8’s ‘What’s Up, Tiger Mommy’, Sam discovered a way to keep the demon in possession of the host body—long enough to vanquish it. He did this by saying the exorcism spell backward—as a result, the demon smoke would go right back into the host, ready to be stabbed with the demon-killing knife.

This isn’t the only time Sam gets inventive with his methods to defeat demons. In an earlier season, he used a PA system to play a recorded exorcism against a group of demons. And in Season 9, he uses a phone recording of the spell to stop a demon when she grabs him by the throat, which prevented him from chanting the spell out loud.

Sam Winchester? More like Smart Winchester, amiright?

5. Sam Undergoes the Heavenly Trials

Since Season 1 of Supernatural, Sam and Dean Winchester have been looking for ways to shut the door on hell permanently. In Season 8’s ‘Trial and Error’, the Winchesters finally get the chance they’ve been looking for.

Prophet Kevin (Osric Chau) spends his time deciphering the word of god and finds the key to closing the gates of hell permanently—three Trials of God. The catch? Only one person can undergo the trials.

Of course, Dean decides that he must be the one to undergo the Trials, seeing as they’re dangerous and potentially fatal. But while on a mission to achieve the first Trial, it is Sam who completes the quest of killing a hellhound.

Rather than try and summon another hellhound so Dean can kill it, Sam makes the valiant decision to undergo the Trials himself, no matter the cost to his body.

It is an easy decision, at first. Sam achieved the first task with aplomb and even though the actual Trial caused some pain, he seemed well-equipped to continue to the next two.

But the second Trial took more out of Sam—so much so, that Dean had to step in and stop Sam from going out hunting in a weakened state.

Despite the agony he was in, Sam continued to push forward for the third and final Trial, knowing that he could possibly die in the process.

But having seen his brother sacrifice himself repeatedly, Sam was ready to step up to the plate and be the one to make the sacrifice play. And this remains one of the most endearing aspects of his personality.

4. Sam Confesses to Letting Dean Down

It is at the end of the Trials of God, that fans were treated to an excellent moment of character development for Sam Winchester.

As the younger of the Winchester brothers, Sam hasn’t had to make that many hard choices—he literally left Dean in purgatory to live a normal life. On the one hand, that’s exactly what Dean told him to do. On the other hand, why would you not look for your brother even if they said otherwise?

Dean was, unsurprisingly, a little cheesed off at being left to rot in purgatory while Sam lived his life, and this misstep clearly haunted Sam during the Trials of God.

During the third Trial, his body severely depleted, and his mind focused on the task at hand, Sam learns that completing the Trial won’t just close the gates of hell, but will kill him in the process. In a shocking moment that fans will never forget, Sam’s response to this revelation is “So?”.

The Winchesters have always been fighters and they always want to go on living—Sam makes a point of mentioning that at the start of the Trials. But everything that Sam goes through in the course of the Trials makes him realize how many times he has failed Dean.

In fact, his last confession is about his failure to be a good brother to Dean—Sam legitimately believes that Dean would be better off without him because Sam hasn’t done enough to save his Dean.

The entire confessional scene between Sam and Dean is heart-wrenching and powerful—and it’s made all the more memorable by Dean’s valiant attempts to bring Sam back from the edge. That Sam chooses to continue to live and accept his brother’s forgiveness shows just how willing he is to learn more and to grow.

3. Men of Letters = 0, Sam Winchester = 1

Most fans would agree that the British Men of Letters (BMoL) were kind of the worst. They appeared to be allies of the Winchesters—they certainly had the same goals to kill monsters—but they rubbed everyone the wrong way.

But they did have some fantastic gear that made fighting supernatural creatures that much easier—if only it didn’t come with the condescension and a general lack of empathy.

Fans weren’t all that surprised when it turned out that the BMoL weren’t as good as they purported to be. From teaching their young students to game the system by literally murdering their friends, to becoming obsessive about their codes and rulebooks, the BMoL proved that they were just another bureaucratic machine that needed oiling.

While both Dean and Sam went up against the BMoL together, in the end, Sam led their hunter friends in an all-out attack on the BMoL base. Sam had a structured plan—having studied the layout during his time with the BMoL—and was efficient in the execution of the plan.

In the end, the BMoL were demolished, and all remaining Winchesters were reunited—having learned a valuable lesson about whom to trust.

Never one to hold a grudge, Sam even used his time with the BMoL to power his next moves. Sam has always exemplified the Men of Letters legacy of the Winchester family, and he shows as much when he uses some of the BMoL’s techniques to organize his own group of hunters in Season 14.

2. Jack Finds a Father Figure in Sam Winchester

New characters are hard to adjust to, especially in a show as long-running as Supernatural. But the inclusion of Jack Kline, the child-like, world-unaware Nephilim son of Lucifer and Kelly Kline (Courtney Ford), was a welcome injection of humor, naivete, and suspense.

While Jack worked hard to be recognized as a member of the Winchester team, he had more trouble with some members than others.

Castiel pretty much adopted Jack as his son once Kelly passed away and the two continue to share a close bond. But the Winchester brothers—with their long and difficult history with Lucifer, were much wearier of Jack. Or rather, Dean was.

Sam has had a propensity for giving people—even monsters—second chances. He had a Kitsune friend, Amy Pond (Jewel Staite), who was forced to kill to keep her son alive. Knowing the reasons for her actions, Sam let her go—only for Dean to kill Amy later, thus causing a rift between him and his brother.

Throughout the show, Sam has reacted by trying to save people and monsters as a first course of action—resorting to killing when necessary. He did whatever possible to save his partner Madison, who was turned into a werewolf, only killing her when there was no saving her.

It isn’t surprising that Sam saw beyond Jack’s heritage to acknowledge the person he was. Unlike Dean, who saw Jack’s powers and legacy as a threat, Sam was ready to give the boy the leeway he needed to grow into a good human being.

Not surprising, considering Sam’s abilities had caused his loved ones to distrust him for years—his psychic abilities, and his strength from drinking demon blood had made him a pariah. Sam being Sam, he stood by Jack and gave him all the chances he needed, even if it meant opposing Dean’s cynicism.

Eventually, even Dean came around to accepting Jack and the four members of Team Free Will 2.0 were able to continue their work as hunters.

1. Sam Convinces Dean Not to Go into the Box

Season 14 of Supernatural saw Dean becoming the vessel of Michael from an alternate universe—a fate he had fought for years—to finally destroy Lucifer.

While Dean managed to overcome Michael eventually, and with Sam’s help, kept Michael locked up in his mind, Dean was looking at a lifetime of struggling for control—and the inevitable breaking down of walls that would allow Michael to take over his body again.

Dean finally accepts that stopping Michael means disappearing somewhere where Michael can’t hurt anyone. Death/ Billie (Lisa Berry) shows Dean how to create a Ma’lak Box—the only thing powerful enough to contain an archangel.

For Dean, the plan is simple enough—lock himself in the box and throw it in the bottom of the ocean forever.

While that sounds perfectly reasonable when you know that the alternative is Michael walking the Earth and leaving nothing but ashes in his wake, this plan doesn’t sit well with Sam.

Sam gives an impassioned speech about believing in Team Free Will—that they have and will save the world. He refuses to believe that they have no other choice than giving up because they never give up, and that’s why they’ve made it so far.

It’s a wonderful scene that doesn’t get a beat wrong—and eventually, Sam convinces Dean to let them come back to fight another day.

If there’s one thing Sam Winchester is great at, it’s believing the best of people and the world. His optimism has wavered from time to time, but he always finds a way to pick himself and everyone around him back up.

Saying goodbye to the Winchesters, Castiel, Jack, and their friends is going to be difficult for fans of Supernatural. But if this list has shown us one thing, it’s that this show has so many wonderful, memorable moments.

November 2020 may be the end of the show, but these moments will live on forever with Supernatural fans.

There you have it, folks—Sam Winchester’s best moments on Supernatural. Which moment is your favorite? Tell us in the comments below.

Supernatural Season 15 will air on The CW from October 8.

Louis Skye

Louis Skye (Ronita Roy Mohan) is a contributor at FlickSided and a Tomatometer-Approved Critic. A writer at heart with a fondness for well-told stories, Louis has honed eir pop culture writing over 15 years and is currently the Managing Editor of 3-time Eisner Award-winning WWAC. E always has an eye out for the subversive and champions diversity in media. Pronouns: E/eir/em or She/her/hers Louis' podcast, Stereo Geeks, is available on all major platforms.