Top 10 Best Sam Winchester Moments on Supernatural
Top 10 Best Sam Winchester Moments on Supernatural

Top 10 Best Sam Winchester Moments on Supernatural

VOICE OVER: Phoebe de Jeu WRITTEN BY: Saim Cheeda
We love these Sam Winchester moments on “Supernatural” almost as much as Dean loves his brother. For this list, we'll be looking at the most memorable, funny and/or touching moments of the younger Winchester sibling from this dark fantasy series. Our countdown includes his case of bad luck, possessed by Lucifer, beconciling with this father, and more!

No wonder Dean loves his Sammy! Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Sam Winchester Moments on Supernatural.

For this list, we’ll be looking at the most memorable, funny and/or touching moments of the younger Winchester sibling from this dark fantasy series. With fifteen seasons worth of adventures, there’s a lot of laughs, tears, and good times that Sam has provided fans over the years.

#10: His Case of Bad Luck
“Bad Day at Black Rock”

When he comes across a rabbit’s foot, it seems as though Sam’s gotten luck on his side for once. Unfortunately, it turns out the foot is cursed to kill the user with bad luck if it’s stolen. As the Winchesters’ luck would have it, Bela Talbot snags it away and poor Sammy’s on the receiving end of a world of awful mishaps. With everything working against him, he spends the rest of the episode tripping and stumbling over anything in his way, making him absolutely useless. The crowning moment of hilarity arrives when Sam gets his foot stuck on a grate as he tries to free himself. Having lost his shoe, he can do nothing but look like a helpless little boy who’s just done with life.

#9: His Awful Acting Skills
“The French Mistake”

There’s no doubt that Jared Padalecki has some serious acting chops, but the same can hardly be said for Sam. Too bad for him, as in this fan favorite episode he had to channel his inner Jared, and it was something he failed miserably at. After he and Dean are sent to an alternate world where Supernatural is a TV show, they realize they’ll have to play their parts. However, acting doesn’t naturally come to either brother, and they end up making fools of themselves. Sam in particular has great difficulties in remembering his lines, and his improvisations are only successful in being unintentionally laugh-out-loud. It doesn’t get any better with repeated takes, as Sam’s obsession with the key and the lock ruins filming for good.

#8: His Reluctant Killing of Madison

Sam has arguably more heart than his older brother, as he’s been shown to be willing to let even monsters live if proven innocent. Heartbreakingly, in this case it’s his newfound love Madison who asks him to take her life. While they originally start off as mere acquaintances, Sam and Madison’s emotional connection ends up becoming an intimate one. However, after it’s clear that Madison is a werewolf, they’re left with no option but to go with the worst case scenario. Although Madison accepts her fate, a distraught Sam is unable to hide his sadness, yet he still volunteers to be the one to pull the trigger. Seeing his little brother in such a state even brings Dean to tears, with Sam showing remarkable courage with having to end his lover’s life.

#7: Possessed by Lucifer
“The End”

Considering Sam is Lucifer’s true vessel, it’s no surprise that they share multiple standout moments. There’s Season 7 during which the Devil tortures Sam to near insanity with hallucinations, with some painful but unforgettable scenes. (xref) Before this however, we see what a fully empowered Sam/Lucifer pairing would be like in an alternate future that Dean gets sent to. Here, Sam seemingly has no regrets about consenting to Lucifer’s possession, as the latter openly boasts to Dean about gaining his victory. It’s fitting to see Sam embrace his dark side, though, as his good intentions only led to ruin. While it’s Lucifer who brought the world to his feet, it’s clear Sam feels a certain measure of catharsis.

#6: When He Stepped Up as a Leader
“Who We Are”

The character development of Sam Winchester has to do with him accepting his destiny as a hunter. Once the British Men of Letters solidify themselves as a threat, it comes up to Sam to rally his allies to launch an assault against the enemy. When it seems as if the other hunters are having second thoughts, Sam brings up an impassioned plea to reach out to their hunter spirit. Not only does this change their minds, but he also convinces them to follow his lead into war. As he succeeds in his plans to take the British Men of Letters down, Sam completes his transition from reluctant hero to a proven leader.

#5: Becoming Whole Again
“The Man Who Knew Too Much”

Sam spends the first half of Season 6 pretty much the villain due to his soul being left in the cage. “Soulless” Sam has no emotions and no care for Dean. Even after Death brings Sam’s soul back, the memories of his time in Hell remain behind a mental wall - that is, until Castiel causes it to break. Faced with no other option, Sam is forced to confront “pieces” of himself to be revived. Here, we watch as he soldiers through the pain of his memories, as the real Sam has to fight his soulless state once again. The most noteworthy moment takes place at the end of his journey, as Sam accepts his tortured self back just so he can return to his brother again.

#4: Confessing His Failures to Dean

Season 8 brings a number of internal conflicts between the brothers. While they do team up again, the estrangement makes Sam recall the times he’s failed Dean. With the trials to close the gates of Hell almost complete, he comes close to sacrificing his life when Dean interrupts him. However, Sam reveals that he deserves to die, as his overwhelming guilt makes him believe he isn’t worth saving. He also confesses his pain at seeing Dean seeking comfort in other characters like Castiel and Benny over him, showing true vulnerability after a long time. This admission goes a long way in confirming how Sam does look up to Dean, and how much he wants to make his brother proud.

#3: Reconciling with His Father

Unlike Dean, Sam grew up defying his father’s orders time and again, voicing his resentment of the hunter life. After John once again tries to keep the brothers in the dark, Sam goes so far as to pick a fight with his own father. This memory comes back to haunt him after John’s death, as he regrets leaving things off in such a way. Over a decade of carrying this guilt, Sam finally gets a chance at reconciliation when the time-displaced John arrives in what is the future for him. Despite John acknowledging his mistakes as a parent, Sam overlooks his failures and instantly forgives his father. After witnessing just how bitter he’d once been with John, it makes for a heartwarming moment to see Sam in his father’s arms.

#2: Offering to Trade His Soul to Save Dean
“I Know What You Did Last Summer”

Sam has taken any chance he can to rescue his brother from trouble, no matter how difficult it might be. This is why, when Dean trades his soul for Sam’s resurrection, the younger Winchester is wracked with guilt. Rather than accept his new lease on life, Sam begins a tireless attempt in season 3 to get Dean out of his contract, killing anyone connected to it throughout. Few moments highlight this more than in this season 4 flashback, where he’s seen distraught after Dean’s eventual death and is so broken down that he becomes desperate to get his brother back. Despite knowing the kind of punishment Lilith would have for him, Sam’s perfectly willing to trade places with Dean and go to Hell forever.

Before we unveil our top pick, here are a few honorable mentions.

Getting Hopped Up on Medication
“Sam, Interrupted”

Celebrating Christmas with Dean
“A Very Supernatural Christmas”

Dean’s Overdramatization of Sam’s Personality
“Tall Tales”

Fanboying Over Castiel
“It's the Great Pumpkin, Sam Winchester”

Having Faith in Dean
“Point of No Return”

#1: Overpowering Lucifer
“Swan Song”

In Season 5, the fate of the world came down to Sam, with the love for his brother allowing him to overcome the devil. After having enough of Dean’s constant interferences, Lucifer, while possessing Sam, decides to beat Dean to death. With the Apocalypse hanging in the balance, Lucifer is on the verge of landing the killing blow. However, the sight of an old toy in the Impala triggers Sam’s memories, flashing him back through warm memories he’s shared with Dean. In the span of a few seconds, we see Sam’s childhood play out, and how he shaped up to be the man he’s become. Through these memories, Sam’s able to wrest back control from Lucifer, before making the ultimate sacrifice by leaping into Hell.