Funniest Dean Winchester Quote in Season 1
Deputy: So, fake US Marshall, fake credit cards. You got anything that's real?
Dean: My boobs...
Dean: I hope your apple pie is frickin' worth it!
Dean: Where's our father, Meg? Meg: You didn't ask very nice.
Dean: Where's our father, bitch?
Dean : Dude, you fugly.
Dean : That fabric softener teddy bear... oooh, I'm gonna hunt that little bitch down.
Dean: Aww, what's the matter Sammy? Afraid you're gonna get a little Nair in your shampoo again?
Dean: Eat me. No, no, no wait, wait, wait, you actually might
Sam : What makes you so sure?
Dean: Well, because I'm the oldest, which means I'm always right
Sam : Where are you?
Dean: In the middle of nowhere, with a killer truck on my ass!
Dean : [to Wendigo] Hey, you want some white meat, bitch? I'm right here!
Dean: Well, I've got a yorkie upstairs and he pees when he's nervous.
Dean : Sam? Marry that girl.
Dean : You mean like protection against demons salt? Or, uh, oops I spilled the popcorn salt?
Dean : Oh, we're going for it, baby. Head spinning, projectile vomiting, the whole nine yards.
Dude, stow the touchy-feely, self-help-yoga crap. It's not helping!
Dean : Why do they make it so hard to steal from dead people?
Sam : Find anything?
Dean: Besides a whole new level of frustration? No.
Dean : Do me a favor, next time you see one, pay attention. When someone says a place is haunted, don't go in.
Dean : Vampires. Gets funnier every time I hear it.
Sam : I don't understand, Dean. We burned the damn thing! Dean: Yeah, thank you, Captain Obvious.
=============================================================================Funniest Dean Winchester Quote in Season 2
FBI Agent Victor Henricksen: You think you're funny?
Dean: I think I'm adorable.
Dean : My name is Dean Winchester. I'm an Aquarius, I enjoy sunsets, long walks on the beach and frisky women.
Dean: Yeah, MySpace, what the hell is that? No seriously, is that like, some sort of porn site?
Dean : L.A. A young girl got kidnapped by an evil cult.
Sam: Yeah, and does this girl have a name? Dean: Katie Holmes
Dean : I like him. He says "okey-dokey."
Dean : Of course the most troubling question is why do these people keep assuming we're gay?
Dean : Dude, I full on Swayze-d that mother.
Dean: We were hunting the djinn. Sam: The gin? You're drinking gin? Dean: No, asshat, the Djinn, the scary creature.
Dean : It takes two to... you know... have hardcore sex.
Dean : There's tons of stuff on unicorns to, in fact I've heard they ride on silver moon beams and shoot rainbows out of their ass.
Dean : This is humiliating. I feel like a freakin' soccer mom!
Dean: Neil, it's your grief counselors. We've come to hug.
College Professor: Son have you been drinking?
Dean Winchester: Everybody keeps asking me that but no.
Dean : You know what, you're right. Come here, I want to lay my head gently on your shoulder. Maybe we can cry, hug, maybe even slow dance.
Mark: My neighbor... Mr. Rogers?
Dean: You have a neighbor named Mr. Rogers?
Dean : Don't go surfing porn, that?s not the kind of wacking I mean.
Dean : You see me mucking around with crystals and listening to Yanni?
Dean: Dude, your like a walking encyclopedia of weirdness.
Dean : Bring me some pie! I love me some pie!
Dean : Sam, I think I know what we're dealing with here... It's the Stay Puff Marshmallow Man
=============================================================================Funniest Dean Winchester Quote in Season 3
Dean : I'm Batman.
Dean: You fudging touch me again I'll fudging kill you!
Dean : What's in the box! Brad Pitt? ...Seven? ... No?
Sam : So you two were talking a case?
Dean: No we were talking about our feelings, and then our favorite boy bands.
Dean: Nobody kill any virgins!
Bela: You know, when this is over, we should really have angry sex.
Dean:...Don't objectify me.
Sam: Well, I'm thinking about fairy tales.
Dean: Oh, that's nice. You think about fairy tales often?
Dean : I'll tell you one thing - there's no way I'm kissing a damn frog.
Dean: What are you going to tell me next, the Easter Bunny's Jewish?
Ruby: It's called witchcraft, shortbus.
Dean: You're the shortbus...shortbus...
Sam: Man, I had a weird dream.
Dean: Yeah? Clowns or midgets?
Dean: Gumby Girl...does that make me pokey?
Dean : Ok, Weirdy McWeirderson.
Dean: Aw, don't go away angry, just go away
Dean: I'm going to stop the big bad wolf, which is the weirdest thing I've ever said.
Dean: I guess my ass is too sweet to let out of sight.
Sam : Yesterday was Tuesday, right? But today is Tuesday, too!
Dean: ...Yeah, no, good, you're - totally balanced.
Dean: A Hand of Glory? I think I got one of those at the end of my Thai massage last week.
Sam: A Crocatta.
Dean: What's that? Some kind of sandwich?
Dean: I'm just gonna ask it again -- who was that masked chick? Actually, the more troubling question would be, how come a girl can fight better than you?