Single Perfect Tear

A classic single perfect tear in "The End."

Dean Winchester has displayed an affinity for crying a single perfect tear.

This is sometimes referred to as the “Single Emo Tear of Manly Angst” (which originated on TWOP) or variations thereof.

At Jus In Bello Italy 2011 Jensen revealed the crew referred to this phenomenon as the OPT - "One Perfect Tear."

It is unknown if this ability is in any way related to Jensen's Wonky Eye.

Dean Winchester’s Single Perfect Tear List

2.02 Everybody Loves a Clown

The first time we see the Single Man Tear is in the scene where they are burning John’s body. Sam and Dean have just lost their father, who had sacrificed himself so Dean could live, leading to Dean crying.

2.04 Children Shouldn't Play with Dead Things

During an emotional moment, Dean confesses that he thinks he should be dead and his Dad should still be alive, resulting in a tear slowly making its way down his face.

2.17 Heart

When Madison, a werewolf who got close to Sam, has to be killed to stop her from attacking and killing others, Dean offers to kill her but Sam wants to do it himself. Dean is upset and sad that Sam has to kill someone he cares for and Dean gets emotional, leading to him crying.

2.20 What Is and What Should Never Be

Dean visits John’s gravesite and talks to him, asking why he always has to be the hero and save the people. Being tired of always being the one to sacrifice something leads to Dean shedding a tear.

2.21 All Hell Breaks Loose: Part One

Sam dying in Dean's arms is more emotional than many other things throughout this show but seeing the look on Dean’s face as he holds Sam’s body close to him and cries is too much.

2.22 All Hell Breaks Loose: Part Two

Sam is dead and Dean is talking to his body. He tells his brother how much he feels like he failed Sam and why he should have done better. The whole speech Jensen gives is super intense and leads to us seeing Dean cry.

4.03 In The Beginning

When Dean travels back in time and meets his mother Mary as a young woman, he has to be around her without letting on that she is dead in his future, but he can’t do it. He ends up crying when he tells her not to get out of bed on the night in the future when she ultimately dies.

4.10 Heaven and Hell

While explaining to Sam what Hell was like and that he wishes he could no longer feel anything, Dean completely breaks down, but still only sheds that one lonely tear. The emotion in his face and the serious look Sam gives him leads to a supercharged scene.

4.16 On the Head of a Pin

Dean is in the hospital when he finally realizes he is the one who broke the first seal that started the apocalypse. Not thinking he is strong enough to survive what is to come, Dean sheds a tear.

4.21 When the Levee Breaks

When Dean realizes that Sam is so messed up and he can’t fix it, Dean gets upset and cries. Knowing that Sam is so far gone on Demon Blood that Dean feels like he can’t save him is too much for Dean, who always looks out for Sam.

5.04 The End

Dean is sent into the future and, upon seeing that Lucifer takes over control of his brother and kills future Dean, our Dean sheds a tear. He knows that if he doesn’t do something to change things, this is where they will eventually end up.

5.10 Abandon All Hope...

Writer Sera Gamble said, “Abandon All Hope... was the first time I actually cried watching a director’s cut. At first I thought maybe I was just having one of those days, but I checked in with the other writers… I don’t want to incriminate anybody, so I will just say that one or more male producers also shed what we like to refer to as A Single Perfect Man-Tear.”

9.01 I Think I'm Gonna Like It Here

Dean resorts to real prayer to any Angel to save Sam who is about to die. This is an act of desperation like no other and leads to Dean getting very emotional and shedding a tear.

9.09 Holy Terror

Gadreel has been lying to Dean while possessing Sam and has just killed Kevin right before Dean’s very eyes. Feeling like Kevin was his responsibility and knowing that technically Sam’s hands just murdered their friend leads to Dean thinking he failed, again. The look on his face as he cries is heartbreaking.

10.15 The Things They Carried

The One Perfect Tear is not actually in this episode, but in Supernatural: The Musical!, with the song "A Single Man Tear", sung by the actors portraying Sam and Dean. In it, "Sam" reflects that Dean hides his emotions, afraid of how others see him, while "Dean" acknowledges the repression of his feelings out of fear of his inability to forge his own path.

11.17 Red Meat

This episode is a big bundle of pain, but the Single Man Tear that shines through is the one where Sam has just died, and Dean is lost without his brother. We know what Dean feels like when he loses Sam but doing so as unexpectedly as he does here is different.

11.21 All in the Family

While technically this scene is a double tear, it still fits. Dean is talking to God about the way He treated and abandoned Sam and Dean. This parallel between God and John Winchester both letting Dean down leads to his tears of disappointment.

12.11 Regarding Dean

In this episode, Dean loses his memory. At one point, he is in the bathroom reciting things, trying to remember the rapidly-fading basic facts of his life. The tear that crosses his cheek and the look of abject horror on his face once he realizes he doesn’t know who he is anymore is shocking.

12.22 Who We Are

Dean finally realizes that everything he has gone through and what his childhood was is not his fault, that he should have been able to just be a kid without the issues and stresses that John being a hunter brough into his life. He tells his mother as he cries that he hates her and loves her because he knows life would be different if she had lived.

13.21 Beat the Devil

While in an alternate world full of pain, Dean is forced to tell his own mother that Sam, her baby boy, has just died. The shock on his face as he realizes she has to know is heartbreaking, but the lone tear that slides down his face as he tells her the truth is too much.

14.19 Jack in the Box

While not a single man tear, the emotional crying river of tears Dean gives as he sobs his heart out in sitting in the middle of field in the rain after Mary's wake.

15.09 The Trap

Dean is attempting to find an ingredient they need to hopefully defeat Chuck, while back in Purgatory. He has been separated from Castiel and prays to him. where he apologizes for his anger and fear getting in the way of their friendship, and forgives him for his role in Mary's death with tears in his eyes.

15.18 Despair

After Castiel sacrifices himself to save Dean, the guilt Dean has for his part in Castiel's death causes him to break down in tears.

15.20 Carry On

Dean has finally gotten his freedom from Chuck controlling his life and continues to hunt. Losing to a nest of vampires, Dean knows he is going to die and gives an amazing speech about how much his life has meant to him and making sure Sam will continue on without him. The last thing Dean does before entering Heaven is shed a single man tear in his brother’s arms.

Similarly, when Sam dies of old age. He too sheds a single man tear after his son tells him it is okay to go.