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Single Perfect Tear (also known as the One Perfect Tear)
 
This was really meant for Dean, and lord knows he’s made a trademark of it.  There's the very famous closing shot in "Heart"...
 
HeartDeancries
 
Or the one that still makes me bust out crying to this day, Dean's speech to dead Sam in "All Hell Breaks Loose Part Two"...
 
Deanspeech12
 
Then there's another one of my favorites, when Dean confronts Samifer in the future in "The End"...
 
Deanweeps
 
However, even Sam has been known to pull off a few single perfect tears as well, especially in the later seasons.  In the earlier seasons his tears were sloppy wet messes.  The one that gets me the most is Dean dying in his arms in season nine's “Do You Believe in Miracles?”
 
SPN 1590 
 
Isn't it any wonder that the Single Perfect Tear got it’s own song in season ten's “Fan Fiction?"  These lyrics to “Single Man Tear” are so wrong they're right.  
 
A Single Man Tear
 
(Sam sings)
A single man tear slips down his face
He shows emotion without a trace
He hides behind a mask so strong
Worried that he could be wrong
I wish that he could see the way I see him
The perfect brother, a man without sin
Cause underneath the manly sheen
It is my brother, a boy named Dean
A single man tear, a single man tear, a single man tear, that’s all we fear
 
(Dean sings)
A single man tear, that’s all I’ll spare
I bury feelings, don’t show I care
Even though I am haunted, must be the man daddy wanted
Wish I could be as strong as Sam
Blaze my own trail, be my own man
But underneath this broken mask
It is my father, with all his wrath
A single man tear, a single man tear, a single man tear, that’s all we fear
 
 
As you can tell, this wasn't a comprehensive look.  I only scratched the surface!  Are there any unmentioned scenes from one of these bits that stands out for you?  Please share and fondly recall twelve seasons worth of golden material along with me.  
 
A big huge thanks to Supernatural Wiki for all their wonderful pages on these bits, right down to the episodes that include them.  It made this article a ton easier!