|Relationships:||Older brother of Sam Winchester, older half brother of Adam Milligan-Winchester, son of Mary and John Winchester, etc.|
|Other:||Played by the actor Jensen Ackles as an adult, by Ridge Canipe as a child, by Brock Kelly and Dylan Everett as a teen, and by Chad Everett as an elderly man.|
|Click here for related articles on Fanlore.|
Dean Winchester is one of the three main characters of the long-running television series Supernatural. Dean and his younger brother, Sam, hunt demons, werewolves, vampires, and other supernatural creatures across the United States. Their best friend Castiel also helps sometimes. They are frequently in conflict with the forces of Heaven and Hell, sometimes aided by their frenemy Crowley.
Dean has been described as confident, brash, crude, protective, brave, emotional, sensitive, adventurous, obedient, loyal and witty.
Canon Character Arc
Eric Kripke has said that he modeled Dean off of Star Wars character Han Solo. In seasons one and two, Dean's character arc involved reuniting with his younger brother Sam after several years, their search for their missing father, and their ongoing hunt for the demon that killed their mother and Sam's girlfriend. Dean's motivation in the first two seasons is to protect Sam and to make sure that he doesn't succumb to darkness and Azazel's plans for the other children who possess psychic abilities.
Dean's devotion to his family is showcased, including his guilt over his father, who sold his soul so Dean would live. At the end of season two, Sam dies unexpectedly, and Dean decides that he is unable to live without Sam and sells his own soul to a crossroads demon to bring Sam back to life. At the end of season three, Dean dies and goes to Hell as stipulated in the deal. The angel Castiel resurrects him in season four, and he angsts about having spent part of his time in Hell torturing other souls and enjoying it.
Seasons four and five show the breakdown of and attempted repairs to Dean's relationship with Sam. Dean resents his role in the grand master plan for the world. It is discovered in season five that Dean is meant to be the vessel for archangel Michael in order to defeat (or kill) Sam, who is the destined vessel for Lucifer. Dean and Sam's relationship parallel's Michael and Lucifer; like Dean, Michael is the dutiful older brother. Because Dean refuses to be a vessel, Michael uses Dean's younger half-brother, Adam, instead. At the end of season five when Sam jumps into the pit dragging Michael/Adam in with him and sacrifices himself to save the world, Dean lives a normal life with Lisa and Ben for a year (until Sam returns in season six).
In season eight, Dean gets stuck in Purgatory with Castiel and Benny.
In Fanon and Fanworks
Dean is frequently noted for crying prettily, including often shedding a single perfect tear, as evidenced in several picspams. He is often the ultimate woobie in the majority of Supernatural fanworks, and in reviews of especially woobie-riffic fic, he may be referred to as D:ean (sadface D Dean).
Many Supernatural fanfic writers write gen stories with a strong focus on the close, intense, emotional brotherly (but non-sexual/non-romantic) relationship between Sam and Dean.
In regards to top/bottom dynamics (mainly regarding anal sex) within most Supernatural fanfic, Dean is generally portrayed as the bottom/uke, including in both slash and het fic. In Wincest fanfic, the majority of fics and fanfic writers frequently portray Dean as the bottom/submissive/gentle partner and Sam as the top/dominant/aggressive partner. There are many different reasons as to why Dean is frequently portrayed as the submissive/bottom in the overwhelming majority of Supernatural fanfic, but some of the reasons for this could include Dean being given the established role of nurturer, protector and caretaker of people (mostly of Sam since childhood), being the obedient, loyal son who followed his father's orders, Dean frequently shown to be emotionally sensitive, vulnerable and fragile and his submissive, gentle sexual style/canon sex scenes on the show with women.
Dean's most frequent and popular slash pairings in fanworks are Sam/Dean aka Wincest and Dean/Castiel. Dean/Castiel first appeared in fanwork after the angel Castiel was introduced in season 4 and later became a series regular. Dean/Castiel is also known as Destiel. A more recent ship is Dean/Crowley, aka Drowley, which became more popular after season 10.
Dean is also paired with the Impala (see Dean Winchester/Impala pairing page), both in circumstances where Sam was possessing the Impala, and where the car was just the car. Sometimes Dean is paired with both Sam and the Impala. 
Dean is also featured in het fic, with the most frequent pairings consisting of Dean/Jo and Dean/Lisa.
In some fanfictions and fanvideos, Dean gets paired with Elena Gilbert from The Vampire Diaries.
Bisexual Dean Winchester
There are many fans who headcanon that Dean Winchester is bisexual, while others view him as a heterosexual character. Discussion about Dean's sexuality, and canon evidence for and against these headcanons (and others) have been around since the early seasons of the show. More recently the debate about Dean Winchester's sexuality has lead to accusations of queerbaiting, and questions about whether shipping fans have unrealistic expectations, or are unfairly denigrated for pointing out the queer subtext.
I saw a video of a girl at a convention who was super sweet and she asked Jensen something about if he thought Dean might be bisexual and people actually booed her and Jensen refused to comment on the topic and I heard that she actually left the panel because she was so hurt and upset. That’s not ok. I understand that a lot of people don’t ship Destiel, I happen to be one of them, but no one can deny that the writers of this show have written so many scenes where it makes it look like Dean and Cas have a relationship that could likely have romantic feelings. [...] I couldn’t care less whether someone ships it or not, but no one in this fandom should ever be made to feel like their less of a person or beneath anyone else for where they want these amazing characters to end up.
I seriously don't think Dean is bi in canon. It's been refuted more times than officially confirmed by either text or the staff themselves. That being said, write all the fic you want! Make all the lovely fanart! (I've done it myself!) Unfortunately, there has been a very vocal part of fandom that has jumped on TPTB about "queerbaiting" (that ill-fated #AskSupernatural fiasco, anyone?), and THAT in part is what has left a stain on the fans who tend to be more flow about their fandom behavior. You can read Dean as bi if you wish, but demanding that he be actualized concretely on the show is what tends to get fandom in a tiz.
- Fans take Supernatural to task for 'Queer Baiting' article on advocate.com, detailing the #AskSupernatural fiasco, July 2014.
- ‘Supernatural’s Scariest Monster: Bisexual Erasure' by Hannah Johnson, article on Bitch Flicks, posted September 2016.
- Why Dean Winchester’s Bisexuality Matters by Marty Stu in Culture, TV & Movies, on fanslashfic.com, posted September 2016.
- Dean Winchester is the Bisexual Hero Supernatural Deserves by Mary Sue in Culture, TV & Movies, on fanslashfic.com, posted August 2018.
- Feeling Good
- Broken (Dean) by Luminosity (streaming versions at Critical Commons)
- Dean & John - Because of You by MissStabler
- Dean Winchester: Ex's and Oh's by Roarkshop
- The one who always go out and blaze a glory style(Dean Winchester) by chaotic aRina
- Dean Winchester - Gettin Bi by AngelDove
- Dean Winchester - I'll be good by AngelDove
- Dean Winchester - My Demons (Video/Song request) by AngelDove
- I'm past saving/Dean Winchester by Amelia
- i bring the fire - dean winchester by sparksfly221
- dean winchester ; me too by salindore
- - Dean Winchester || one look & you're mine by surrealistic
- Protect and Survive, May 2006 essay on Dean Winchester by marinarusalka at Idol Reflection
- It is Easier to Build Strong Children than to Repair Broken Men: Dean Winchester and Early Years Education (Archived Link), by LookAtTheseFreakingHipsters (2013)
- The Subversion of Dean’s Masculinity by defilerwyrm (2013)
Additional Art Gallery
- Dean Winchester page at the Supernatural Wiki
- Best of Dean Winchester Quotes collection of certainly funny and amazingly inspiring quotes.
- Supernatural Fic on Delicious tagged with Dean
- Dean Winchester works on ff.net
- Dean Winchester works on AO3
- Dean-fic, a Livejournal community
- Dark!Dean, a LiveJournal community
- TV Trope A Single Tear
- Such as Dean crying Picspam! by moondropz 12 November 2009, (Accessed 25 April 2011) and 20 Favourite Dean Winchester Faces by bellanut, 12 December 2007, (Accessed 25 April 2011).
- Works tagged Impala/Dean Winchester at AO3.
- Works tagged Impala/Dean Winchester/Sam Winchester at AO3.
- Comment by Akayes on fangasmthebook.com article, April 2014.
- Comment by reddit user sulphurcocktail, September 2016.