Dean Winchester is the older of the two Winchester brothers in the CW cult fantasy drama Supernatural. The series has had an incredible run of 15 years and the actors, like their characters, have practically grown up with the show.
Supernatural. He started out as something of a mischievous older brother who wasn't mature enough for his age and was definitely more immature than his more serious, intellectual younger brother Sam. From the cheesy tough guy and an incorrigible flirt, Dean has had a significant developmental arc over the years. Here's how he transformed in the span of 15 long years.
The Cheesy Older Brother In Season 1
When Dean Winchester first made an entrance in season 1, he was the sarcastic, fun older brother to young Sam who was gearing up for a promising future with a steady girlfriend.
Dean was a much simpler character at the time than the relatively more complex Sam. He loved fast food, pies, and women. And god knew he had no trouble getting the latter with his extraordinary good looks. He didn't have big plans for himself, and usually just went with the flow. But there was one person in the world he felt deeply responsible for and that was his little brother.
The Good Son In Season 2
Dean's devotion to his brother was matched only by his devotion to his father, who he respected grudgingly even though he was well aware that John Winchester hadn't been an ideal father to either of the brothers.
Yet, Dean knew what his family (and especially his dad) had been through following his mom's death, and for all his tough exterior, he was ready to follow into his dad's footsteps and obey at him as best as he could. In season 2, John turns up and entrusts his older son with Sam once and for all, although Dean had taken up that mantle years ago. Dean is still funny but his deeply emotional side started coming to the fore in season 2.
Season 3's The Quintessential Tough Guy With A Secret
In season 3, Dean is still trying to keep up appearances for Sam but this time he has a secret, he is being torn apart inside by the prospect of dying at the end of the year. He had made a deal with a crossroads demon to exchange Sam's life for his own in the season 2 finale and has only a year to live in season 3.
In season 3 the brothers are also on the run from the law as well as trying to round up as many demons that had been released through the Devil's Gate, as possible. So there is a lot going on, as usual, but Dean has to maintain his don't care attitude despite what he is going through emotionally.
Brother's Keeper In Seasons 4 & 5
Dean is back from Hell in season 4 and pretty badly shaken up, although once again he wouldn't let Sam see him in his vulnerable state.
In seasons 4 and 5, Dean is desperate to try and save his brother, whatever the stakes. The fight to keep the Devil from being unleashed is on. However, for all the trauma the older Winchester has been through during his time in Hell, he makes a new friend who is destined to become his only and best friend in the world, the angel Castiel.
Trying To Keep It Together Through Seasons 6 & 7
In Seasons 6 and 7 the show loses its initial grasp of the plot somewhat and goes a little haywire. Sam is back soulless from Lucifer's cage in Hell, and Dean along with the ever-loyal Bobby is trying to keep it together as his brother wreaks havoc and suffers from hallucinatory episodes as the Devil gets inside his head from time to time.
Dean here has had a taste of what life could be like if they just lived as ordinary people with the people they loved. So it took him strength to leave all that behind and go off hunting monsters again with his brother. In season 7, the brothers suffer their biggest tragedy yet with Bobby's shocking death and Dean has to come to with that as well. The relatively more mature arc of the character is very clear here.
Grown As A Person In Season 8
Dean is back from Purgatory in season 8 and has visibly grown as a person. In Purgatory, he has had experiences that have left him scarred, and the failure to save Castiel and bring him back to earth weighs down on him.
Dean's relationship with Sam is also a bit choppy now as he learns of Sam's lack of effort to look for him during all the time he had been gone. However, with so much of ugly going on, he has still got one or two true friends, like the vampire Benny who he had met in Purgatory. Dean from the earlier seasons wouldn't have thought twice before killing a vamp, but the fact that he respects and appreciates Benny's honesty shows how much he has grown.
Dark & Tormented In Seasons 9 & 10
Trying to save the world has its kinks. In season 9, Dean, Sam, and Cas are up against the Knight of Hell, Abaddon, and team up with the snarky King of Hell, Crowley, to beat the slimy demon; things take a sharp turn for the dark as Dean act-first-ask-questions later mentality gets him saddled with the terrifying Mark of Cain.
The whole of season 10 is probably one of the darkest in the series yet, with Dean being at the center of the drama. His inherent goodness and strength of character comes through with a vengeance as he fights the Mark with everything he has. Gone is the insanely funny quintessential Dean moments and in his place fans see a more arrogant, deeply troubled, and violent Winchester brother.
Locking Horns With Apocalyptic Forces In Season 11
Sam and Dean lock horns with forces of apocalyptic nature in season 11 as the Darkness is set free once the Mark of Cain is removed from Dean's arm.
Dean finds himself conflicted as he is inexplicably attracted to Amara. He is at the same time determined to go on fighting, for there is really nothing else that makes sense to him at this point.
Saving People, Hunting Things In Seasons 12 & 13
In season 12 the brothers fight against their chief antagonist of the season, the British Men of Letters. Dean has finally had some little happiness thrown at him as Amara has resurrected Mary, the mother to the brothers Winchester whose devastating death had kicked off the series.
Dean is also hell-bent on distrusting Jack, the Nephilim, and Lucifer's son, who appears for the first time in season 13. Every bone of his body is telling him not to put his faith in Jack, but given his nature, he agrees to give the boy a chance for Sam and Cas's sake.
Whatever It Takes In Season 14
The 14th season began with Dean in a whole new avatar, possessed by the archangel Michael, the secondary antagonist of the season, besides Lucifer of course.
Actor Jensen Ackles was seen in a different light altogether as his character had evolved from the clumsy, at times hysterically funny Dean to the much more serious, darker, more poignant, and definitely more mature Dean.