Oh, thank you season eight!  Way to bring the word "character" back to Dean Winchester.  For a guy that's been through so much, he was finally able to take many steps forward in his growth, and the end result is someone I believe in again.  

For anyone that read my "Deeper Look at Season Seven Dean Winchester," I was pretty damned annoyed over the butchering of his character by the end of the season.  Of course they didn't so Sam much justice either, but with Dean, it was a guy I didn't recognize.  Here's an excerpt from that article that has particular impact on my season eight analysis:

I so wish I could say that season seven continued in this same vein, with Dean finding enough of his fighting spirit and love for his brother to handle the numerous obstacles that came his way.  Sadly, Dean spent a majority of the season apathetic and depressed, going through the motions without any fire or desire to carry on the family business.  He certainly didn't open up to his brother, which rendered the once tight brotherly bond stale.  We waited all season for him to finally get the kick in the pants he needed and slip out of his funk, but he never did.  

I bring that up because I everything that I wished for in season seven Dean happened in season eight.  Now this is the Dean Winchester I remember!  He wasn't a sorry drunk that was depressed and going through the motions.  It got personal, and Dean reacted with a new resolve and commitment to who he is - a hunter and a loyal brother.  There's no doubt about it though, this is not season one Dean.  He is more mature, grounded, and focused.  

Season eight was a tale of two seasons.  The first and second halves were dramatically different, but each had a major importance to Dean's overall character growth.  As I've done with each "Deeper Look" segment, I'm going to go through the episodes and show Dean's progression through the season.  Overall, it's a lot more refreshing and satisfying than what we've seen in a while.  However, there's so much goodness to examine this year, that for the first time I'm breaking up this study into two parts.  Part one looks at the first half of the season, part two will look at the dramatically different second half.  

We Need To Talk About Kevin

I kind of see this as Dean on a major roid high and being forced to come down.  His year in Purgatory certainly kept the adrenaline going, so his hyped up reaction to Sam and everything else was perfectly understandable.  However, this did kick off the big controversy, aka Sam making the deliberate choice not to look for Dean during that year and Dean's livid response to that.  Dean will end up not letting Sam forget about this for several episodes.  

Dean has come back with some baggage of his own though, and Castiel is clearly part of that.  He dodges Sam's questions about how he got out and about Cass, just giving the dodgy answer "I saw enough."  He's definitely a guy going through a rough transition, much like a soldier who has come home after war.  The memories of Purgatory are still very fresh and swarming inside him.  Those memories are of Benny, his comrade in arms.  It's possible that his devotion to Benny became stronger when he returned, just because of his disappointment over Sam.  

It's upon reuniting with Kevin though that Dean's new purpose is cemented.  It's their chance to send every demon back to Hell, to get back at them for destroying their lives.  They have to do that, no matter what the cost.  That cost of course involves Kevin and Sam, who must forget their hopes of a normal life and become part of that crusade.  

Dean:  If this kid is right, he's sitting on a bombshell.  Hell, he is the bombshell.  What?
Sam:  That.  There's no way that Kevin is getting out of this intact, is there? 
Dean:  Well, he's doing pretty well for himself so far.
Sam:  He got out.
Dean:  And now he's in it, whether he likes it or not.  
Sam:  So, freewill, that's only for you?
Dean:  I can't believe what I'm hearing.  Sam, we have the opportunity to wipe the slate clean.  We take Kevin to the tablet, he sends us a spell, we send every demon back to Hell forever.  Every single bastard that destroyed our lives.  That killed our mother, killed Jess...and you're not sure? 

Dean may be sure, but how far will his hellbent focus go?  Who is he willing to sacrifice?    He's certainly not going to sugarcoat things, or offer hope to Kevin like Sam did.  "Alright listen to me, I'm sorry about your girlfriend, okay, I am, but sooner you get this the better, you're in it now, whether or you like it or not.  You gotta do what you gotta do."  Ouch, on the nose much Dean?  
What's Up Tiger Mommy?

Meet the new, hard edged Dean Winchester.  He's still raw, and has a new FBI interrogation technique.   No dealing, more strangling and threatening with a knife.  He's the guy that will kill Kevin Tran's mother to serve the greater good.  Except I do believe that Dean forgot that the knife didn't kill Alastair, so why would it kill the King of Hell?  It would only kill Mrs. Tran.  But that's a quibble that has very little to do with our hero and more to do with a writer that didn't check his facts. 

Here the focus of Dean's guilt shifts to his memories of Castiel in Purgatory.  The encounter with Samandriel the angel triggers some of this.  He isn't letting that guilt hurt his mission though, and explains to Sam that he would have killed Mrs. Tran just because it was Crowley, no matter who's in the meatsuit.  "Yeah, it would have sucked and I would have hated myself, but what's one more nightmare, right?"  This is rather far from the Dean of earlier seasons who always drew lines when it came to innocents getting killed.  


Aside from Dean throwing more guilt trips at Sam about quitting hunting, and him not accepting Sam's talk of going on without him, there wasn't much else to see here.  It was a blip that ruined the great character groove going from the previous two episodes.  Given the fact the writers were Eugenie Ross-Leming and Brad Buckner, that explains it all. 


There may not be much Sam and Dean in this one, but I loved seeing the two from the outsider's perspective.  Dean does say "awesome" too much (don't we all?).  But the biggest take away we got from this with Dean is he's not so far gone in his black and white thinking that he'll kill an innocent who hasn't harmed yet.  It's a reflection of the chance he's giving Benny.  A big drama that's about to play out.

Blood Brother

No doubt about it, the brothers are really on edge with each other right now.  They're at each other's throats.  Dean ditches Sam during their hunt for Kevin without explanation after a call from Benny.  He won't tell Sam why, he just goes.  It's interesting how Benny is someone that deeply matters to Dean, but Dean can't share anything about him to Sam.  Can't or won't?  Is he trying to protect Benny, knowing that Sam will be against the idea of Dean letting a monster live, or is it something else.  A trust issue perhaps?  

Sam and Dean are at odds, no doubt about that.  They aren't on the same page regarding Kevin, and Dean's questionable actions when trying to kill Mrs. Tran.  He certainly isn't going to let Sam off the hook.  "Last I counted you took a year off from the job.  I need a day."  One bitchface from Sam shows how much that comment isn't appreciated.  

With Benny though, Dean's entire attitude changes.  He's supportive, and will not turn away from his friend's needs.  He refuses to leave without helping Benny, making sure whatever he's up to won't get him killed.  He will stand by his new "brother" through thick and thin.  Plus we get a great "vampirates" joke!  The final scene though is chilling enough.  Dean and Sam are reunited at the dock with bitter stares, and when Sam figures out that Benny is a vampire, it's one head shake from Dean that tells it all.  Benny is a friend and will not be harmed.  Benny knows these two have a lot to talk about, but it only ends with brothers throwing angry glares.  They couldn't be farther apart on things right now.  

Southern Comfort

I strangely liked this episode.  It's usually the type of heavy handed stuff that launches my primal screaming for the season (luckily I didn't have to use that until "Man's Best Friend With Benefits"), but there was a logic to the way this storyline was approached.  The characterization was actually well done.  I know the whole "being under truth mind control" story is really contrived at this point, but we know with Dean it usually takes a scenario like this for him to be brutally honest with the truth.  Sam needed that brutal honesty.  We all did really.  His passive-aggressive approach with Sam not looking for him that year was getting rather tiresome. 

Dean brought up all the greatest hits.  "Because everything you've done since you've climbed into my ride has been to deceived me."  Sam drinking demon blood, running off with Ruby, not mentioning the fact he didn't have a soul, and running around with Samuel for a year letting him think he was dead.  Then of course, the big zinger, not looking for him that year all because of a girl.  This little dig at Sam didn't seem important at the time, but it plays big later.  "Benny's been more of a brother to me in the past year that you've ever been!  That's right, Cass let me down, you let me down, the only person that hasn't let me down is Benny." 

Dean actually did get a valuable lesson from this episode, and suddenly Garth has aged years in wisdom.  I've always loved Garth's easy going and simple approach to life.  He reminds Dean he can't change the past, and Sam is all he has.  He has to let it go.  It's very nice to see after this, Dean does and is slowly on his way to taking a protective role again with Sam.  I don't think Dean minded looking at things that way for once.  That's despite the fact that Sam rips into him at the end, issuing the ultimatum to move on or he will.  Dean agrees to move on with no argument.  Of course he doesn't like Sam's threat to Benny, but they'll cross that bridge when they come to it.  And oh do they come to it.  

A Little Slice of Kevin

Dean is on better terms with Sam, and that turns his attention back to Castiel.  It's meant to be the resolution to this whole dodgy guilt trip thing over trying and failing to save Castiel in Purgatory.  Dean has never handled guilt well, and obviously failing to bring Cass out of Purgatory with him weighed heavy on his conscience.  

Castiel's sudden and unexplained appearance, triggered two issues for Dean.  First, how did Castiel get out?  From his experience, that was a near impossibility.  He remembered every second of getting out.  It's hard to forget.  So Dean has to wonder, what is Castiel not telling him?  He's even being open with Sam about his reservations, so that's a step in the right direction.  

Of course, that's all part of the bigger issue, the one that's been eating away at him since he got back.  What happened back there?  How did he fail?  Dean goes through more memories in Purgatory, and even though he suspects Castiel let go, or didn't fight hard enough, he still believes what happened was his fault.  Dean believes his inability to help Cass was just another one of his failures.  "Look, I don't need to feel like Hell for failing you, okay?  For failing you like I fail every other God forsaken thing that I care about.  I don't need it."  

Luckily Castiel was there to set the record straight.  He reminds Dean he can't save everyone, even though he tries.  This wasn't Dean's fault.  He let go.  He was there for penance and didn't want to leave.  He didn't know how to tell Dean he didn't want to be saved, and everything can't be Dean's responsibility.  At the end though, Castiel's confession doesn't really make Dean feel better.  If anything, it makes him more suspicious about his friend.  

Hunteri Heroici

Dean:  What's the word Cass?
Castiel:  A short version of my name. 

Hee, I never tire of Castiel's fish out of water literal responses.  Setting that aside, Dean and Castiel do share a nice heart to heart.  Dean's obviously worried about his friend, given his mysterious return from Purgatory, and wants to help.  As much as he wants to see Castiel return to Heaven, Castiel's devastation over all the pain he caused in Heaven is a good reason not to go.  

Citizen Fang

Dean finally has to make that choice, Sam or Benny.  Sam has crazy Martin tailing Benny, and Martin is ready to play executioner just because Benny is a vampire.  Dean needs to look into it, and finally deal with any suspicions he has of Benny.  He believes Benny's story, he wasn't killing innocents, and helps him with his plan to get the person doing all this, but Sam and Martin don't believe Benny, despite Dean's reassurances.  Cuffing him to the radiator was probably not the best choice.  So Dean has to take action that will protect both Sam and Benny, because he knows each are very capable of killing the other.  It isn't pretty, but Dean will do what he has to do to get results.  

Dean obviously saw this coming thanks to Sam's words at the end of "Southern Comfort," and as we find shockingly at the end of the episode, he had a backup plan in place.  Sam during the hunt for Benny gets a mysterious text from Amelia to come quick, and he flies out of town.  That just leaves Benny and Martin, and Dean knew who would come out on top of that one.  Benny was stronger.  

There's ramifications for his actions though, and that's clear when Sam figures it out in the end.  Dean was the one that sent that text and has made his choice, protect his friend over trusting his brother.  Sure, Dean thought he was protecting them both, but Sam didn't take it that way.  Sam took it as a betrayal.  Dean sternly accepted what he did as right, and that he didn't have much choice.  His action drove Sam away though, and Sam stayed in Texas while ignoring Dean's calls.  

Torn and Frayed

Dean goes to Texas to get Sam, but their first encounter is mired in frustration.  Dean thinks Sam only heard what he wanted to hear, that Benny killed Martin.  Benny wasn't killing people, and killed Martin in self defense and defense of his granddaughter.  Sam can't believe that Dean is going with that story, but Dean says it's the truth.  "There was a time when that all meant something."  

Sam confesses why Dean's act is so harmful.  That text set off a major fear in him, that the woman he loves was in harms way.  Everything that happened Jessica, to everyone they cared about might have happened to Amelia.  Sam poses the question that gives Dean a whole new perspective.  "Is that what we are?  You save a vampire by making me believe that the woman I love might be dead?"  Dean isn't sure what he has to say to make it right.  All Sam had to do was trust him.  Sam tells Dean he wanted him to trust Benny, and he couldn't do that.  So Sam gives the ultimatum.  Dean needs to be done with Benny.  He doesn't know if he can or not and leaves.  

Sam ends up facing his own ultimatum with Amelia.  She will choose him, but he has to be all in.  He has to choose her over everything else (aka Dean even though Sam didn't tell her he was alive).  While Sam and Dean struggle with their choices, they've got to help Castiel (well, Castiel kind of forces Sam to help in rather hilarious fashion).  They need to rescue Samandriel.  

Kevin offers Dean some perspective when Dean finds out he sent his mom away.  Kevin called her a distraction.  He needed to focus.  He can't enjoy a world that he needs to save.  This is more important.  Castiel offers the other perspective, with one simple phrase.  "I need both of you to stow your crap."  

Through working together, Sam and Dean figure out how much they rely on one another to cover their backs.  It's Castiel's strange behavior though, especially his murder of Samandriel, that they realize they're into something too deep.  Dean is still willing to let Sam choose happiness with Amelia over the job and handle it alone.  Sam needs to know why.  "I don't know. I'm just tired of all the fighting.  Maybe I'm a little bit jealous.  I could never separate myself from the job like you could.  It's time for at least one of us to be happy."  Sam isn't sure, so Dean makes it clear.  Both feet in or out.  "Anything else will get you dead."  

While Sam goes off to decide, Dean makes his choice and calls Benny.  End of the line.  He's going forward, with or without his brother.  Luckily, Sam chooses to stay, although he looks miserable.  Dean is there in support, offering a silent "are you alright?" and Sam nods back looking pretty glum.  It's bittersweet, but the brothers have chosen each other.  Now they can move forward.  

LARP and The Real Girl

After this episode, I wanted to send writer Robbie Thompson that fruit basket.  This is classic, funny, loose, dedicated hunter Dean Winchester at his absolute best.  I smile thinking of how this whole whacked out situation was something that Dean adjusted to quickly, much like his prison stay in "Folsom Prison Blues."  He even went for the whole medieval outfit, chain mail and everything.  

Dean's found a little sister he can talk to and share everything in Charlie.  He tells her about what he did to Sam with the text message.  She reinforces to him how wrong that was.  With all the madness between Sam, Benny, and Castiel, a confidant and friend to share his problems is exactly what he needed.  But it was a chance for him and Sam to start square too, and this time Dean wanted to do a bit more than the job.  He wanted to have fun, like they used to.  Eventually, Sam comes around, know how much it means to Dean.  

Honestly, does it get any better than this?  Braveheart Dean for the win!  

In looking at this progression, the first part of the season was crucial in getting Dean ready to handle the big responsibilities of the second half, aka the Men of Letters legacy and getting Sam and Castiel through trials that they could not face alone.  

Coming up, it's part two of the tale of two season eights. It all leads to multiple Dean character defining moments, rather exciting ones for our hero, not to mention a restoration of the brotherly bond that's so been missing in prior seasons.  Dean becomes quite the hugger!  Maybe Garth was rubbing off on him after all.  

For my other "Deeper Look at Dean Winchester" segments, they can be found here:

A Deeper Look at Supernatural Season Seven Dean Winchester
A Deeper Look at Supernatural Season Six Dean Winchester
A Deeper Look at Supernatural Season Five Dean Winchester
A Deeper Look at Supernatural Season Four Dean Winchester
A Deeper Look at Supernatural Season Three Dean Winchester