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Yes, this article did sit in my WIP folder for two years, only to see the light of day because I was sharing the other four on twitter for fun and then realized this one was missing.  Yes, I’m also aware seasons six and seven have passed us by in that time too.  I clearly have some catching up to do. 

What can you say about season five Dean Winchester?  He was angrier, far more depressed, and perhaps his sharp tongued comments fell a bit more on the bitter side.  It’s still classic Dean though, no matter how you look at it.  So let’s go through the episodes and fondly remember, the wisdom of Dean Winchester, season five.   


Sympathy For The Devil

The elder Winchester was a little dour in this one, and with good reason.  After all, little brother betrayed him with Ruby and then “accidentally” let Lucifer loose.  They didn’t exactly cover this one in hunting school.  Not to mention, some very powerful angels are on his tail.  So what happens when they follow through with their clue from Chuck and it’s trap at John’s old lockup by said angels?  A Dean Winchester classic, that’s what (and one of my favs).

“Oh thank God, the angels are here.”

Dean isn’t done yet.  The chips are down, Bobby is paralyzed, but he isn’t giving up.  At least not in front of Bobby.  He saves the “that was crap” speech for Sam. 

Dean:  What if we win? I'm serious. I mean, screw the angels and the demons and their crap Apocalypse. They want to fight a war, they can find their own planet. This one's ours, and I say they get the hell off of it. We take 'em all on. We kill the Devil. Hell, we even kill Michael if we have to, but we do it our own damn selves.
Bobby:  And how are we supposed to do all this, genius?
Dean:  I got no idea. But what I got is a G.E.D. and a "give 'em hell" attitude and I'll figure it out.
Bobby:  You are nine kinds of crazy, boy.
Dean: It's been said.

Good God Y’all

What do you do when you score a horsemen’s ring? 

“So, pit stop on Mt. Doom?”

 
Free To Be You and Me

A Dean Winchester fiesta of great lines!  All with Castiel, but they’re great nonetheless.

“You were wasted by a Teenage Mutant Ninja Angel?”

So, what, I'm Thelma and you're Louise and we're just going to hold hands and sail off this cliff together?

“Last time you zapped me someplace, I didn't poop for a week. We're driving.”

Dean:  We're humans. When we really want something, we lie.
Castiel:  Why?
Dean:  Because--that's how you become president.

Dean:What is that?
Castiel:It's oil. It's very special. Very rare.
Dean: Great. So we're gonna trap Raphael with a nice vinaigrette?
 
There are two things I know for certain. One: Bert and Ernie are gay; two: you are not gonna die a virgin, not on my watch.”
  
The End

Again, it’s Dean and Castiel, but it’s classic.  

"You know it's kinda funny talking to a Messenger of God on a cell phone. It's like watching a Hell's Angel ride a moped."

Also, what’s the best way to convince your future self that you’re you?  Bring up something you’d never share with anyone.  Good thing Sam never heard this story!

Rhonda Hurley. We were, uh...19. She made us try on her panties. They were pink. And satiny. And you know what? We kind of liked it.”
 
Fallen Idols

Gotta love when Dean Winchester get to be snarky with the inside joke.  

Dean: Hate to break it to you, lady, but I'm no Paris Hilton BFF. I've never even seen House of Wax.
 
I Believe The Children Are Our Future

What else can you say when you just cooked a ham with a joy buzzer? 

That'll do, pig.”

The Curious Case of Dean Winchester

It's Grumpy Old Men done the Supernatural way.  Out of the awesome exchange between Bobby and old Dean in the graveyard, this line is my favorite...

Pound it up your ass, Ironsides.

Once Dean's back to his old self though, he gets to knock some sense into his elder for once. 
 
 
You don't stop being a soldier 'cause you got wounded in battle. Okay? No matter what shape you're in, bottom line is, you're family. I don't know if you've noticed, but me and Sam, we don't have much left. I can't do this without you. I can't. So don't you dare think about checking out. I don't want to hear that again. 

Changing Channels

THIS is Dean Winchester at his finest, calm and professional after what is clearly the nuttiest situation on earth.  

Dean:  We're sure it was. But see, it helps us to hear every angle. So just tell us what you thought you saw.
Kathy:  It's impossible, but...I could have sworn I saw...the Incredible Hulk.
Sam:  The Incredible Hulk.
Kathy:  I told you it was crazy.
Dean:  Bana or Norton?
Kathy:  Oh, no, those movies were terrible. The TV Hulk.
Dean:  Lou Ferrigno.
Kathy:  Yes.
Dean:  Spiky-hair Lou Ferrigno.
Kathy:  Yes.
Dean:  Huh.
Kathy:  You think I'm crazy.
Dean:  No. Uh, no, it's just...is there, uh, would there be any reason that Lou Ferrigno, the Incredible Hulk, would have a grudge against your husband?

THIS is Dean Winchester at his finest, NOT calm and professional after what is clearly the nuttiest situation on earth.  

“Calm down? I am wearing sunglasses at night. You know who does that? No-talent douchebags. I hate this game. I hate that we're in a procedural cop show and you wanna know why? Because I hate procedural cop shows. There's like three hundred of them on television and they're all the freaking same. It's ooh, plane crashed here—oh shut up.”

The Real Ghostbusters

Dean still is a bit on edge, but wouldn’t you be if a couple of chuckleheads were badly re-enacting your life?  

“No, I'm not a fan, okay. Not fans. In fact, I think the Dean and Sam story sucks. It is not fun, it's not entertaining. It is a river of crap that would send most people howling to the nuthouse! So you listen to me. Their pain is not for your amusement. I mean, you think they enjoy being treated like-like circus freaks?”

Comments  

anonymousN
# anonymousN 2012-08-03 02:23
I did not know about the Wisdom of Dean Winchester articles. Thanks for this article and the links to the previous ones.All the lines were pure gold..Funny,sca ry..all were perfectly delivered by Jensen .
PaintedWolf
# PaintedWolf 2012-08-03 02:30
I absolutely love this, thanks Alice. I may have to go back and read the other ones again, too. Man, I wish you could actually say even half of what comes out of this man's mouth in real life without getting your ass kicked!
I also noticed the "when I come back". Jesus, I would have run away screaming too.
Oh, and my whole family knows "Pudding!"
Jayne Lamb
# Jayne Lamb 2012-08-03 04:28
GREAT article. But does anyone else think Dean would have been bored stiff by the LOTR movies? :lol:
alysha
# alysha 2012-08-03 06:38
These were funny. Looking at all the pictures reminds me for the umpteenth time, that Dean makes faces that remind me of Deniro's. Look at the pic from episode 3-5.
Ginger
# Ginger 2012-08-03 08:43
Gosh, Alice, this was great. I didn't know about the DW Wisdom articles either. Off to read the rest of them.
Sylvie
# Sylvie 2012-08-03 15:22
In the words of the coolest dude ever, Awesome. I will surely be checking out the past Dean wisdoms.
Amy
# Amy 2012-08-04 17:53
That speech Dean gave to Bobby at the end of Sympathy for the Devil.......... ......I would have followed Dean anywhere...even to Hell.

To learn mere moments later that it was all bunk? That he didn't mean one word? I was as disappointed as Sam. The way Sam's face fell...was me. I realized right then that Dean didn't believe in anything. He didn't believe in his own family/friends. he didn't think they were good enough... to get the job done...or to do the job That he would say whatever he felt... I felt manipulated and betrayed by him.

I geuss it explains why Dean surrounds himself with Angels and Demons these days. He doesn't consider them weak like he does humanity....lik e he does sam. Dean has said numerous times to Sam that his empathy and compassion make him weak. "all that wussified crap" as he told Souless Sam. Makes you wonder if Souless Sam deciding to actively prevent regaining his soul was a careful manipulation by Dean. That is until he proved he was too dangerous for Dean to control.

So he decided to get the weaker version back...the one he was able to control and manipulate
Cindy
# Cindy 2012-08-04 22:49
Someday, it would be interesting to watch whatever version of Supernatural you're watching, because we're clearly not watching the same version.
LEAH D
# LEAH D 2012-08-05 21:52
Respectfully disagree. I think Dean's speech was to bolster Bobby. Nothing more. He still has trust issues with Sam at that point, and is not in a good place, but I am not sure why you felt so betrayed. I do not think Dean thinks humans and Sam are weak. Just my opinion. I agree with Cindy that we must be watching different versions of SN.
ryder21
# ryder21 2012-08-10 06:38
What a wise man Dean is! Alice, can I add two of my Dean wisdoms that always tickle me?
In SFTD when Meg kisses him, Dean licks his lips and asks "What is that, peanut butter?"
And in Sam Interrupted after Dean has his first therapy session with his psychologist, Sam encounters a disturbed Dean who states he has just been 'thraped'. Classic Dean that always cracks me up.

In regards to the speech Dean gave at the end of SFTD, I must say that I totally agree with Cindy and Leah D. Dean has faith in humanity, he was just in an uncertain place at the time, and was attempting to reassure Bobby (and maybe himself) with a bit of Dean bravado.