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.  

jensen ackles

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. 

vlcsnap 00004

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

1.03 0080 Dean Profile full pic

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. 

SPN 1335

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

vlcsnap 00068

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. 

12.09 96 Dean Lt

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."

IMG 0492

Click *Next* for Dapper Dean! 

Dapper Dean

Shedding his flannel, Dean cleans up really well! From 7.12 "Time after Time" (#ThankyouRobbie!)


Dean's expression might not be the best but the tux certainly deserves an honorable mention! From "Red Sky at Morning" 3.04.

vlcsnap 00032

Take your pick: light reflecting in his eyes, full cowboy look; or lurking in the shadows sideways glance! Either way, Dean's western cosplay in "Frontierland" 6.18 is mysterious and engaging! Ride-em, cowboy! 



Can you resist a man in uniform? Dean puts your resolve to the test in "Pac-Man Fever" 8.20. 
8.20 0092 Dean Uniform

No collection of Dean's best looks would be complete without his perfectly fitted undercover suit, tie and overcoat. This shot frames Dean beautifully, as is befitting the episode - "Regarding Dean" 12.11.

(Lest we stray too far into the shallow end of the pool, your assignment, should you decide to accept it, is to find a gif from 8.08 "Hunteri Heroici" when Dean walks away from the camera to go over to talk to Castiel. It provides ample testimony of the perfect fit of Dean's suit!) 

Michael!Dean's impressive, confident presence in cap and multi-layered proper attire is cinematically framed in a mesmerizing shot, with the long, empty alley of light as a backdrop.  From "Stranger in a Strange Land" 14.01.

SN1401a 0165b

Returning to the halo effect depicting the theme of angels' impact on Dean, Michael!Dean shows off his Heavenly perfection in "Gods and Monsters" 14.02. The distinction between Dean and Michael is so evident in this intimidating presence!
SN1402A BTS 0475b

A white tux, top hat and tap shoes? We saved the best for last! From 15.10 "The Heroes' Journey."

15 10 Tap Dancing Dean

The Smiles and the Tears

Dean is known for shedding One Perfect Tear. His grief and pain couldn't (shouldn't) be classified as "breathtaking" but the moment before that tear drops, Dean's anguish grips the heart. This series of shots are some of the most breathtakingly emotional profiles of Dean. 

Deanconsiders22.22  "What Is and What Should Never Be"

vlcsnap 00048
3.01 "The Magnificent Seven" 

7.04  "Defending Your Life" 

6.20  The Man Who Would Be King" 

Thankfully, Dean recognizes the need to balance the tears with some fun. In his all too few lighter moments, Dean's face betrays the impish mischief that is always there, under the surface. Looking into the camera, you can't help but love Dean's "I got you, with a smile" assurance. From "Live Free and Twihard" 6.04. 


We all love it when Dean laughs out loud, whether it be at Sam in glitter or The Three Stooges' slapstick, but this "Yellow Fever" 4.06 post-episode special clip is Jensen's (as Dean) embarrassed yet proud, "That was fun!" smile. Priceless. 

vlcsnap 00127

Click *Next* for Steaming Hot Dean and Just for Fun!

Steaming Hot Dean

That arched back gets me every time! Dean and Anna having one last hurrah in "Heaven and Hell" 4.10.

vlcsnap 00104

Yep, now we all need a cold shower. Dean in "Meta Fiction" 9.18 (#ThankYouRobbie!)

9.18 0042 Dean shower no logo


Demon Dean's antics didn't go unappreciated in "Black" 10.01! 

10.01 Dean Smirk 0311

Just for Fun

Poor Dean. Trapped in a creepy dungeon in a lederhosen in a "Monster Movie" 4.05! 

                                      4.5 0905 Dean Lederhosen                             DeaninLederhosen

Could we even scream that loud if we had to? Voice coaches everywhere are envious! Hilarious! "Yellow Fever" 4.06. 


Dean as a fierce Braveheart warrior? A fanboy's dream comes true in "LARP and the Real Girl" 8.11.


For all his grey steel, dapper, angsty, mysterious, sexy looks, this is quintessential Dean, and the perfect way to end our breathtaking series of Dean. Say it together... "Pudding!" from "Sam, Interrupted" 5.11.

SPN 0479

Those are just a few of the most breathtaking shots of Dean Winchester! Now it's your turn. If there is a shot that you think is absolutely stunning, please share with your Supernatural family in the comments below! 

Next up: Breathtaking Shots of Castiel! 

If Dean is your man, check out our entire category of articles dedicated to Dean