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Poor Sam Winchester. Not only has he had a ton of misfortune and bad luck in his life, but there are often times he finds himself in precarious, utterly humiliating situations which he didn't come close to inviting but has been forced to endure anyway. Sure, several of his little embarrassing messes are the result of his older brother, but isn't that what siblings are for? 

In pouring through all the seasons, I managed to narrow down a lot of Sam's red-faced misfortunes to a less than scientific and totally subjective top twelve. None of these are the result of Dean being a wise ass, so antics from "Hell House," "A Very Supernatural Christmas," and "Playthings" for example won't be seen here. Most of these are outright screwball, reminding us with huge smiles why a big guy is prime material for comedic fodder. 

I originally went for top ten Winchester brother humiliating moments, but I only found one for Dean that's worthy compared to Sam's misfortunes.  As a bonus, his crowing achievement in humiliation will be at the end. I'm sure many of you already know what it is, but remember in guessing, none of these moments are self inflicted (yes, cross "pudding" off the list).

So, without further delay, enjoy these top twelve Sam Winchester humiliating moments (and one for Dean) in order of least to greatest.  

Comments  

anonymousN
# anonymousN 2012-06-07 03:54
All of them were hilarious.Thank you for this article. nothing extra comes to mind about Sam
About Dean how about chased by that small dog in yellow fever
PaintedWolf
# PaintedWolf 2012-06-07 06:32
Hi Alice,

Sam just seems to have the worst luck sometimes, doesn't he? I was cringing for him just reading this. I think you just about covered it.

I, too, have a confession to make, though. I actually love Sam in that ridiculous yellow shirt...
sofia
# sofia 2012-06-07 08:17
Alice, I absolutely loved this! My favorite episode for funny Sam humiliation has got to be Bad Day at Black Rock. Some of Jared's best physical comedy, in my opinion.

Thanks!
KELLY
# KELLY 2012-06-07 10:56
Great list! Hilarious! I think you covered all Sam's. For Dean, Yellow Fever someone mention above and also lederhosen. A lot of them like the red gym shorts, Sam would've been embarrassed by, but Dean took them in stride.
Mickey
# Mickey 2012-06-07 11:14
Heehee, this is so much fun! Poor Sammy!

It made me realize that while they love to stuff Dean in silly outfits and stuff food in Dean's silly mouth, they save the really soul-destroying humiliations for Sam!

And they really love to hit him below the belt too! I'd add Patrick giving Sam the clap in Curious Case to all his below-the-belt woes.

As for the kid in Swap Meat, it obviously wasn't just to get Dean. He wanted out of his scrawny nerdy body and into Sam's (and who can blame him really?) He was trying to escape his life. They even have the big talk at the end where Sam convinces him his life isn't that bad, then as soon as the kid's gone says "No, his life totally sucked."

For the rabbit's foot, he wasn't specifically reaching for it. He was being choked out and was just grasping and groping around for anything he could use as a weapon. The rabbit's foot just happened to be the only thing within reach.

And Becky, well she's resourceful. I'm smaller than she is, and I would've found a way to manhandle Sam into bed, trust me.
Sylvie
# Sylvie 2012-06-08 10:26
Oh my, these were so good, and came at a great time too. I absolutely love your no. 1! Just the look on Dean's face was worth it. And Sam covered in clown glitter was just too good to be true, I still laugh just thinking about it.
nancyL
# nancyL 2012-06-08 19:14
Damn, somedays it just sucks to be Sam Winchester. :lol: :lol:

The worst has to be the Becky episode, from beginning to end. You are right Alice, Dean should have just knocked Sam out and took him somewhere safe. And how did Becky move an unconscious Sam???????
kaj
# kaj 2012-06-09 00:37
Perhaps in Swap Meat, the teenagers decided to swap bodies with Sam because the knew they can't kidnap Dean that easily. I mean the man is scary and also big and executing dangerous aura even if he's calm. He's also 6'2" and those teenagers are cute and tiny. I think they are smart by not hitting Dean full frontal.

But lookie here, who's the guy beside him? He's 6'4" even bigger than Dean. Hmmm I'm sure Sam could out power Dean if he wants to. And also I won't refuse swapping meat with him and objectifying his body like Gary. LOL
ismira
# ismira 2012-06-11 01:26
Gah, so much fun!!! Poor Sammy! All of these moments made me smile, and I remember choking during the cougar-mauling. But hey- I loved Sam in the yellow shirt! I think my favorite is Bad Day at Black Rock, though, it was just way too funny.
As for Dean, I agree that the running-from-th e-little-doggy in Yellow Fever would probably make my list. Oh, and his freak out in Sam, Interrupted. And what could have been a probing table situation in Clap Your Hands If You Believe.
saltwatergal
# saltwatergal 2012-06-12 07:12
Now that someone reminded me of "Clap your Hands..." I remember and crack up with glee the look on our Sammy's face as he lifts that tiny tea cup and innocently asks "do you have bigger cups?" This just knocked me OUT!
Nita
# Nita 2012-06-15 00:30
Good list but for me the most humiliating moment for Dean is a little poodle chasing him at the time when he gets that fear psychosis. That was really funny and Dean acted really well.