At risk of stating the obvious, Dean Winchester has a flare with words. A biting, sarcastic, often snarky sentiment with a flamethroweresque delivery, but clever. Very clever. As Zachariah said in the season four finale, "You're our own little Russell Crowe, complete with surly attitude." I don't know, Russell Crowe doesn't leave me laughing like Dean.  Or wondering with jaw dropped if the boy isn't afraid to let anything come from his mouth. 
In the same guise as my earlier article, "The Enigma of Sam Winchester's Hair," I'm going season by season to remember some of my favorite poetic one-liners rolling off Dean's tongue at those perfectly timed moments. The kind that came freely during disagreements with Sam, in moments of peril, or just laughter in the face of death or trouble. Cute little comments back and forth between the brothers will come in another article. For now, it's Dean zingers galore. After all, deep inside, don't we all relate to Dean's inner 12 year old boy?
Dean won't let a silly thing like being arrested by Chief Wiggum get in his way. When told just how much trouble he was in, Dean wasn't afraid to seek clarification.  Better yet, why not use one of those pop culture references from Deliverance that makes you cringe just thinking about it. 

“We talkin' like misdemeanor kind of trouble or 'squeal like a pig' trouble?”
Aww, Dean can be a supportive big brother too. Dean's recently discovered that his little brother is having troubling psychic visions. After a small time to absorb the fallout, Dean finds an ideal private family moment while searching the Aslyum to get to the heart of the matter.

"Hey Sam, who do you think is a hotter psychic? Patricia Arquette, Jennifer Love Hewitt, or you?"
Dean's flying solo in Burkittsville, Indiana on a missing persons case after he and Sam had a bit of a falling out. Funny stuff has been happening at a nearby apple orchard so he goes to check it out. What could one say after seeing face to face the creepiest scarecrow ever created? Dean knew the right words.

"Dude, you fugly."
Later on, Dean and Emily are prepared for sacrifice to said fugly dude.  Strung to apple trees, they are told their demise is good for the many.  Needless to say, that doesn't go over well. 

"I hope your apple pie is freaking worth it!"
Dean has just been given a death sentence. He lies in the hospital bed, ready to make his peace. Except little brother Sam won't let go. Imagine hearing these sound bites from a dying man on the other side of the curtain:

“That fabric softener teddy bear... ooh... I wanna hunt that little bitch down.” 
“You gotta take care of that car, or I swear I'll haunt your ass.”
"What options? You have burial or cremation."
Route 666
Dean's gone off to deal with the ghost truck, while Sam does some quick research, knowing there isn't much time.  Sam calls up Dean with some info and dares to ask where he is. These might not be words he was expecting to hear.

"I'm in the middle of nowhere with a killer truck on my ass!"
The Benders
Gotta love the dysfunctional redneck family. That gives Dean plenty of golden material to work with, especially when captured through an unfortunate incident involving a frying pan.  This bit of dialogue is so good, I just might as well share all of it.


Pa Bender: I’ve hunted all my life. Just like my father, his before him. I’ve hunted deer and bear—I even got a cougar once. But the best hunt is human. Oh, there’s nothin’ like it. Holdin’ their life in your hands. Seein’ the fear in their eyes just before they go dark. Makes you feel powerful alive.

Dean: You’re a sick puppy.

Pa Bender: We give ‘em a weapon. Give ‘em a fightin’ chance. It’s kind of like our tradition passed down, father to son. Of course, only one or two a year. Never enough to bring the law down, we never been that sloppy.

Dean: Yeah, well, don’t sell yourself short. You’re plenty sloppy.

Pa Bender: So, what, you with that pretty cop? Are you a cop?

Dean: If I tell you, you promise not to make me into an ashtray?

Pa Bender: Only reason I don’t let my boys take you right here and now is that there’s somethin’ I need to know.

Dean: Yeah, how ‘bout it’s not nice to marry your sister?

Pa Bender: Tell me—any of the cops gonna come lookin’ for you?

Dean: Oh, eat me. No, no, no, wait, wait—you actually might.

Of course, the whole incident resulted in one of the most popular taglines in the series.

"I'll say it again. Demons I get, people are crazy!"
The boys just escaped the clutches of Meg, who just took a less than elegant belly flopper out the window. While looking over her supposed lifeless body, Dean finds words of thoughtful advice for his younger sibling:

“Next time you want to get laid… find a girl that’s not so buckets of crazy, huh?”
Dead Man's Blood
Dean believes in a lot of things that are real but Vampires? That's too crazy. Apparently not, for a nest of them have something John Winchester wants.  When it it's time to catch the trail, Dean's still having issues (sorry, couldn't get a clean screen shot on this one).

Vampires. It gets funnier every time I hear it."

Later Dean takes the role of bait for the angry female vampire.  Being a little roughed up actually makes him feistier.

Kate: Car trouble? Let me give you a lift... take you back to my place.

Dean: I’ll pass. I usually draw the line at necrophilia.

Kate: Oh...(Kate

Dean: I don’t normally get this friendly till the second date, but....

Kate: You know, we could have some fun. I always like to make new friends. (She kisses him.)

Dean: Oh, sorry. I don’t really stay with a chick that long. Definitely not eternity.
Devil's Trap
The yellow eyed demon (possessing John) has both Dean and Sam pinned against a wall. While yellow eyes answers Sam's question with full evil swagger, Dean isn't in the mood for a show.

“Listen, you want to just get this over with, huh, cause I really can't stand the monologuing.”
Dean still isn't impressed by the continued taunting and says just the right thing to push yellow eyes over the edge. 

"Yeah, I bet you're real proud of your kids, too. Huh? Oh wait, I forgot, I wasted them."

Oops, this gets Dean a darned good internal organ slicing. 

Coming up, season two.  Dean gets crankier.