1- “I just think it’s really interesting, this sudden obedience you have to Dad. It’s like, ‘Oh, what would Dad want me to do?’ Sam, you spent your entire life sluggin’ it out with that man. I mean, hell, you picked a fight with him the last time you ever saw him, and now that he’s dead, now you want to make it right? Well, I’m sorry, Sam, but you can’t. It’s too little, too late.” — Dean Winchester: Season 2: Everybody Loves a Clown
2- “You’re a freaking child, you know that? Just because you can do what you want, doesn’t mean you get to do whatever you want.” — Dean Winchester: Season 6: The Man Who Would Be King
3- “Mistakes? Well, let’s go through some of Sammy’s greatest hits. Drinking demon blood? Check. Being in cahoots with Ruby? Not telling me that you lost your soul? Or how about running around with Samuel for a whole year, letting me think that you were dead while you were doing all kinds of crazy? Those aren’t mistakes, Sam. Those are choices!” — Dean Winchester: Season 8: Southern Comfort
4- “Details are everything! You don’t want to go fighting ghosts without any health insurance.” — Dean Winchester: Season 4: It’s a Terrible Life
5- “You know, I’m starting to get why parents lie to their kids. You want them to believe that the worst thing out there is to mix some Pop Rocks and Coke. Protect them from the real evil. You want them going to bed feeling safe. If that means lying to them, so be it. More I think about it…more I wish dad would’ve lied to us.” — Dean Winchester: Season 5: I Believe the Children Are Our Future
6- “Why is it my job to save these people? Why do I have to be some kind of hero?” — Dean Winchester: Season 2: What Is and What Should Never Be
7- “Listen, man, I know we’ve had our disagreements, OK? Hell, I know I’ve said some junk that set you back on your heels. But, Sammy…come on. I killed Benny to save you. I’m willing to let this bastard and all the sons of bitches that killed mom walk because of you. Don’t you dare think that there is anything, past or present, that I would put in front of you!” — Dean Winchester: Season 8: Sacrifice
8- “Nothing. It’s just…an angel and a demon, riding in the back seat. It’s like the setup to a bad joke. Or a Penthouse Forum letter.” — Dean Winchester: Season 4: Heaven and Hell
9- “If He doesn’t exist, fine. Bad crap happens to good people. That’s how it is. There’s no rhyme or reason. Just random, horrible, evil. I get it, OK. I can roll with that. But if He is out there, what’s wrong with Him? Where the hell is He while all these decent people are getting torn to shreds? How does He live with Himself? You know, why doesn’t He help?” — Dean Winchester: Season 4: Are You There, God? It’s Me, Dean Winchester
10- “Sam loves research. He does. He keeps it under his mattress right next to his KY.” — Dean Winchester: Season 4: Metamorphosis
11- “I’m not gonna die in a hospital where the nurses aren’t even hot.” — Dean Winchester: Season 1: Faith
12- “My name is Dean Winchester. I’m an Aquarius. I enjoy sunsets, long walks on the beach, and frisky women. And I did not kill anyone.” — Dean Winchester: Season 2: The Usual Suspects
13- “Dude, could you be more gay? Don’t answer that.” — Dean Winchester: Season 3: Bedtime Stories
14- “Come on, man, I know Sam, OK, better than anyone. He’s got more of a conscience than I do. I mean, the guy feels guilty surfing the Internet for porn.” — Dean Winchester: Season 2: Hunted
15- “I usually draw the line at necrophilia.” — Dean Winchester: Season 1: Dead Man’s Blood
16- “Well, there’s pretty much what we do know, that they screwed with financial markets, they helped Hitler get started, along with god knows what else-probably disco.” — Dean Winchester: Season 10: Dark Dynasty
17- “Man, you’ve been holding out on me: this college thing is awesome!” — Dean Winchester: Season 1: Hook Man
18- “You’re a doctor. You’re a medical professional. You’re trying to tell me that my brother’s life is in God’s hands? What, is that supposed to be a comfort? God has nothing to do with this equation at all.” — Dean Winchester: Season 9: I Think I’m Gonna Like It Here
19- “What’re you gonna tell me next? The Easter Bunny’s Jewish?” — Dean Winchester: Season 3: A Very Supernatural Christmas
20- “Yeah, you know how I’m gonna deal? I’m gonna stuff my piehole, I’m gonna drink, and I’m gonna watch some Asian cartoon porn and act like the world’s about to explode because it is.” — Dean Winchester: Season 7: Meet the New Boss
21- “Wow, you get a trophy in Stockholm Syndrome.” — Dean Winchester: Season 7: There Will Be Blood
22- “Three scuzzy bars, one scuzzy strip joint, a chili dog joint, seven or eight nightcaps, and now Scotches in the library. I’m getting cirrhosis just watching this.” — Dean Winchester: Season 6: All Dogs Go to Heaven
23- “Wait a second, do dogs even have ghosts?” — Dean Winchester: Season 7: Defending Your Life
24- “You’re gonna wipe out a whole town for one little witch. Sounds to me like you’re compensating for something.” — Dean Winchester: Season 4: It’s the Great Pumpkin, Sam Winchester
25- “I feel like this whole place is bad-touching me.” — Dean Winchester: Season 6: The French Mistake
26- “That’s crap. You always have a choice. You can either roll over and die or you can keep fighting, no matter what.” — Dean Winchester: Season 2: In My Time of Dying
27- “These aren’t vampires, man. These… these are douchebags.” — Dean Winchester: Season 6: Live Free or Twihard
28- “OK, look. I want a big funeral. All right? I’m talking epic. OK? Open bar, choir, Sabbath cover band, and Gary Busey reading the eulogy.” — Dean Winchester: Season 11: Alpha and Omega
29- “Well, you sure look lovely tonight. Especially for a dead chick.” — Dean Winchester: Season 5: The Real Ghostbusters
30- “Killing things that need killing is kind of our job. Last I checked, taking pleasure in that is not a crime.” — Dean Winchester: Season 9: Alex Annie Alexis Ann
31- “A wise man once told me, ‘family don’t end in blood.’ But it doesn’t start there either. Family cares about you, not what you can do for them family’s there; for the good, bad, all of it. They got your back, even when it hurts. That’s family. That sound like your mother?” — Dean Winchester: Season 10: Inside Man
32- “Oh, you’d like that, wouldn’t you? That’s what that whole speech was about? You’re not afraid to die, are you? You’re afraid to be left in these chains forever. Well, you can sit here and rot, you son of bitch.” — Dean Winchester: Season 9: Meta Fiction
33- “Always knew I’d find the source of all evil at a vegan bakery.” — Dean Winchester: Season 9: Dog Dean Afternoon
34- “So you’re saying we’ve got two super-famous, super-pissed-off ghosts killing their…super-fans?” — Dean Winchester: Season 5: Fallen Idols
35- “Frank, hey, I don’t mean to double-dip in your crazy sauce.” — Dean Winchester: Season 7: Out With the Old
36- “You’re the same thing, only bigger. The same brand of cockroach I’ve been squashing my whole life. An ugly, evil, belly-to-the-ground supernatural piece of crap. The only difference between them and you is the size of your ego.” — Dean Winchester: Season 5: The End
37- “I don’t usually endorse suicide, but, man, what stopped you?” — Dean Winchester: Season 7: Repo Man
38- “Just a couple hours ago, I killed Death. I’m pretty much open for anything.” — Dean Winchester: Season 11: Out of the Darkness, Into the Fire
39- “How does paper beat a rock? It’s stupid.” — Dean Winchester: Season 7: Time After Time After Time
40- “The universe is trying to tell us something we both should already know. We’re stronger together than apart.” — Dean Winchester: Season 10: The Werther Project
41- “Karma’s a bitch, bitch.” — Dean Winchester: Season 6: Caged Heat
42- “You’re either laughing because you’re scared or you’re laughing because you’re stupid.” — Dean Winchester: Season 7: Death’s Door
43- “Demons, I get… But people are crazy.” — Dean Winchester: Season 1: The Benders
44- “Boy, three bedrooms, two baths, and one homicide. This place is gonna sell like hotcakes.” — Dean Winchester: Season 4: Family Remains
45- “I hate these indie films. Nothing ever happens.” — Dean Winchester: Season 7: Of Grave Importance
46- “Somebody goes over Niagara in a barrel, you gonna jump in and try to save them?” — Dean Winchester: Season 2: Crossroad Blues
47- “Leave your name, number and nightmare at the tone.” — Dean Winchester: Season 7: Repo Man
48- “We going to fight or make out, ’cause I’m getting some real mixed signals here.” — Dean Winchester: Season 9: Devil May Care
49- “You know who whines? Babies.” — Dean Winchester: Season 6: Mommy Dearest
50- “Well the problem with the snake is that it has a thousand heads. Evil bitches just keep piling out of the Volkswagen.” — Dean Winchester: Season 4: Criss Angel Is A Douchebag
51- “I mean, accidents just don’t happen accidentally.” — Dean Winchester: Season 6: My Heart Will Go On
52- “Course, there’s nothing more dangerous than some a-hole who thinks he’s on a holy mission.” — Dean Winchester: Season 4: It’s the Great Pumpkin, Sam Winchester
53- “Next time you want to get laid…find a girl that’s not so buckets-of-crazy, huh?” — Dean Winchester: Season 1: Shadow
54- “You know what, there’s a ton of lore on unicorns, too. In fact, I hear that they ride on silver moonbeams, and they shoot rainbows out of their ass!” — Dean Winchester: Season 2: Houses of the Holy
55- “I’m sitting in a laundromat, reading about myself sitting in a laundromat, reading about myself. My head hurts.” — Dean Winchester: Season 4: The Monster at the End of this Book
56- “Secretary’s name is Carly. She’s 23, she, uh, kayaks, and they’re real.” — Dean Winchester: Season 2: Crossroad Blues
57- “Yeah, well, if you were a six-hundred-year-old hag and you could pick any costume to come back in, wouldn’t you go for a hot cheerleader? I would. Mmm.” — Dean Winchester: Season 4: It’s the Great Pumpkin, Sam Winchester
58- “Hey. You know who wears sunglasses inside? Blind people. And douchebags.” — Dean Winchester: Season 9: Dog Dean Afternoon
59- “If this is my last day on earth, I do not want it to be socially awkward.” — Dean Winchester: Season 3: No Rest For the Wicked
60- “I am your brother. See, deep down, I’m just jealous. You got friends. You could have a life. Me? I know I’m a freak. And sooner or later, everybody’s gonna leave me.” — Dean Winchester: Season 1: Skin
61- “I think the world’s gonna end bloody. But it doesn’t mean we shouldn’t fight. We do have choices. I choose to go down swingin.” — Dean Winchester: Season 3: Jus in Bello
62- “Yeah, I’m being an ass and I’m sorry. But right now, we got a freaking zombie running around, we need to figure out how to kill it.” — Dean Winchester: Season 2: Children Shouldn’t Play With Dead Things
63- “C’mon, we hunt monsters! What the hell? I mean, normal people, they see a monster and they run. But not us, no no no, we…we search out things that want to kill us! Yeah, huh? Or eat us! You know who does that? Crazy people!” — Dean Winchester: Season 4: Yellow Fever
64- “You and Dad are a lot more alike than I thought, you know that? You both can’t wait to sacrifice yourself for this thing, but you know what? I’m gonna be the one to bury you.” — Dean Winchester: Season 1: Devil’s Trap
65- “There’s no higher power, there’s no God. There’s just chaos and violence and random, unpredictable evil that comes out of nowhere. It rips you to shreds.” — Dean Winchester: Season 2: Houses of the Holy
66- “I am your flesh-and-blood brother, OK? I’m the only one who can legitimately kick your ass in real time.” — Dean Winchester: Season 7: Hello, Cruel World
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