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.
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.”
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.”
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...
Once Dean's back to his old self though, he gets to knock some sense into his elder for once.
THIS is Dean Winchester at his finest, calm and professional after what is clearly the nuttiest situation on earth.
Dean: Bana or Norton?
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?”