Breathtaking Shots of Supernatural’s Dean Winchester!

If you’ve been following The Winchester Family Business‘ “Breathtaking Photos” series, you know that I’ve had this idea for a while. What if we put together a series of our favorite photos of Supernatural‘s lead stars and characters? I’m not talking about the good pictures, or even the really good pictures, because, let’s be honest, it’s hard for the Supernatural actors to not be attractive in every picture they take! No, I’m thinking about the stunning pictures. The ones that stop you in your tracks. The ones that immediately distract you from what you are doing and demand that you devote your attention to absorbing every light variation, every freckle, every dimple, every pixel of the photo or filmed shot. Would we all choose the same pictures? What exactly makes one image stand out from all the rest? Would all this pretty fill our hearts to bursting? These are important questions that deserve thoughtful answers!

To do this right, we’re creating an appreciation photo stream for each actor and character individually. So far in this series, we’ve shown how talented photographers have captured the breathtaking charisma of Jared Padalecki, Jensen Ackles and Misha Collins. We then turned our attention to the characters they each play on Supernatural, beginning with Sam Winchester! Now it’s big brother Dean’s turn, followed by our beloved angel, Castiel. To find the most breathtaking images of Team Free Will, I reviewed every screenshot, from every episode, from every season aired so far in Supernatural! Weeks of looking at Sam, Dean and Cas pictures to get you the best!

To make sure we don’t miss any of the best shots, we should open this up to the entire WFB family – writers and readers! After you enjoy our collection, you are encouraged to add the pictures that stand out to you! Let’s set some guidelines for your additions:
1. Though it will be hard, hold your favorite pics until that person’s feature! No jumping ahead and cross-posting!
2. Only the person/people featured for each collection may be in the photo.
3. NO MANIPS. Going along with that, no pornographic images.
4. No duplicates. If someone else posts your fave, “love” their posting and go in search of a new fave to add to the collection!

After Supernatural‘s three main characters have had their time in the spotlight, we’ll celebrate breathtaking photos of the friendship between the actors, featuring first Jared and Jensen together (J2), then Jared, Jensen and Misha (J2M). If sufficiently encouraged by your reactions and comments, we can be convinced to continue the series with stunning shots of the Supernatural supporting cast! Let us know who you would like to see next in the line up!

With that all said and done, let’s get started! Here are the most breathtaking shots ever aired of Dean Winchester!

Dean Winchester

Given his personality, it seems fitting to start our collection with Dean’s serious, pensive moments. From the archives, no one does moody like baby Jensen. Dean’s sultry stare and casual James Dean persona make this a classic, breathtaking photo.

Just a few years later, a promotional picture shows a slightly older Dean with the emerging handsomeness of the man he had become by season 6.

Season 9 treated us to the “cage” photo series, with colors and props that teased being trapped between Heaven and Hell… but the tease surely counted on the intentional sub-text!

Season 9 was on a roll! It also gifted us with Detective Dean and his mastery of a suit and fedora.

The season 9 team’s use of lighting created another classic moody Dean photo, with more angst and anger than the picture years before.

Outside of the studio, this has to be one of the most well-known images of Dean Winchester. This “halo aura” moment appeared in “Bloodlust” 2.03.

Although not as well known, this side-lit close up of Dean is equally breathtaking and unique. From Dean’s “Swan Song” episode, “No Rest for the Wicked” 3.16. Take a moment to linger on this pic.

A hint of a smile, or at least passing contentment, in this snapshot from “The Rapture” 4.20, makes this a rare Dean moment.

Lighting, blurred background and Dean’s a wide-open stare combine to capture our attention in “Dead in the Water” 1.03.

A haunted, sideways glance from Dean in “Something Wicked’ 1.18 make it hard to stop staring at this shot, wondering what Dean is thinking in this moment.

Did you just gasp? That’s quite understandable as Dean peers into your soul. From “Devil’s Trap” 1.22.

The dark stillness of this shot conveys Dean’s despair in “All Hell Breaks Loose-Part 2” 2.23. Its mood is inescapable.

In comparison to season 2’s halo shot, five years of long roads, heartache and growing up hard are evident in season 7 Dean’s worried eyes and side-lit, furrowed brow. From “Hello, Cruel World” 7.02.

Dean’s face is so expressive. Yet five more years of pain are behind his look of cold determination in “Stuck in the Middle with You” 12.12.

As a testament to Jensen’s talent, this “First Blood” 12.09 moment of solitude and reflection shows a different kind of determination – resigned, thoughtful.

This stunning image of an angry, pensive Dean is framed by an aura of light that is slightly different than season 2’s halo shot but still reminiscent of Heaven’s interference in Dean’s life. From 14.03 “The Scar.”