Supernatural: 15 best Sam Winchester moments, ranked

"Hello, Cruel World" - Jared Padalecki as Sam Winchester in SUPERNATURAL on The CW.Photo: Jack Rowand/The CW©2011 The CW Network, LLC. All Rights Reserved.
"Hello, Cruel World" - Jared Padalecki as Sam Winchester in SUPERNATURAL on The CW.Photo: Jack Rowand/The CW©2011 The CW Network, LLC. All Rights Reserved. /
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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’.