From the pilot episode, there's a specific moment where Sam refuses to join in the family business on the grounds that it would do no good bringing their mother back and that there's no purpose in searching for their dad, leading to this moment later on:
Sam: Dean, I'm sorry about what I said about mom and dad earlier— Dean: (holds his hand up, cutting Sam off) No chick flick moments. Sam: Alright then... jerk. Dean: Bitch.
En route to the bridge where the monster of the week was last seen, Dean and Sam get into an argument over the music to be played in the Impala before Dean sets the house rules:
"Driver picks the music, shotgun shuts his cakehole."
When Dean is trying to convince Sam to return to go with him:
Sam: When I told Dad I was scared of the thing in my closet, he gave me a .45.
Dean: What was he supposed to do?
Sam: I was nine years old! He was supposed to say "Don't be afraid of the dark!"
Dean: "Don't be afraid of the dark"? What, are you kidding me? Of course you should be afraid of the dark! You know what's out there!
Dean screaming "WHAT A BITCH!" about "that Constance chick" after she possesses his car and tries to run over the brothers, with a tone that suggests that he's really hoping that her ghost heard it.
Dean gets identified as a fake US Marshal by a local cop.
Cop: So, fake US Marshal, fake credit cards....you got anything that's real?
Dean: My boobs.
cut to Dean being slammed against the hood of a police car with a goofy grin on his face
Dean asking if he's in "misdemeanor" kind of trouble or "squeal like a pig" kind of trouble.
"Wendigo" has a specific scene where the brothers are at the local park ranger's office, trying to examine the coordinates found in the last episode. What they end up examining are quite different:
Sam: (looking at a map in the office) Lost Creek, hasn't been touched in years. Plenty of gold and tin deposits around... Dean: (looking at a picture hanging in the wall) Dude, check out the size of this friggin' bear!
"Who said I didn't bring provisions? (whips out giant bag of peanut M&Ms)"
From "Dead in the Water," after Dean's attempts to pick up Andrea backfire on him:
Sam: "Kids are the best?" You don't even like kids! Dean: That's not true. I love kids! Sam: Name three kids you actually know. (Dean stops to think for a moment, occasionally pausing to count on his fingers; Sam waits briefly before going into the motel room they rented) Dean: (following Sam) Hey, I'm thinking!
"Bugs": "Let me just say, we accept homeowners of any race, religion, background, or... sexual orientation."
Twice in 5 minutes.
Dean's reaction to the second time this is said priceless. "Well... I'm going to go talk to Larry. See ya, honey." *slaps Sam's ass*
Special points to the one around 3:14, though you'd only catch it the second time through. The girl? That's Ruby, who knows full well what's going on, though Dean (and the viewers) don't yet. She was doing it just to mess with Sam.
Missouri scolding Dean pre-emptively in "Home." "Boy, you put your foot on my coffee table and I'm gonna whack you with a spoon!" Bonus points for Dean's Reaction Shots - he sounds like such a huffy kid.
"Asylum". In what is otherwise a pretty dark (literally and figuratively) episode, Dean takes a moment to talk to a girl who thought it'd be fun to go see some ghosts in a haunted asylum.
Dean: I got a question for ya. You've seen a lot of horror movies, yeah?
Kat: I guess so.
Dean: [turning to face her] Do me a favor. Next time you see one? Pay attention. When someone says a place is haunted...don't go in!
Dean's utterly unimpressed reaction to the creepy-ass titular villain of "Scarecrow", while the unsettling music plays: "Dude, you fugly."
One particular moment from "Nightmares" (it's a blooper):
Dean: (he and Sam are in sleeve-less priest outfits) Hi, I'm Gene and this is Ace. We're new Chippendale's dancers, we moved in next door. Can we come in?
While Dean is posing as an officer in "The Benders", the lady-cop who's helping him calls him out on it. By telling him the badge he showed her was reported stolen. She then shows him a picture of the real "Officer Washington", who's a fat black guy. And Dean still tries to play it off. "I lost some weight. And I got that Michael Jackson skin disease..."
He gets another one in his tussle against the psycho family. "I’m gonna kick your ass first. (points) Then yours. (gets knocked out)"
Later, they're interrogating him for information.
Dean: Eat me. No, no, wait, wait, you actually might...
In "Shadow", John shows up as the boys get back to their motel.
John: I showed up just in time to see the girl take the swan dive.[beat] She was the bad guy, right?
The prank war of "Hell House" definitely counts. Oh, and the debut of the Ghost-Facers.
In "Provenance", Dean has to break into a mausoleum to destroy a little girl's doll. He drives his car through the cemetery's gates, rams himself through the mausoleum's door, and tries to break the thick glass barrier the doll is in. Hitting it doesn't work, so he searches himself for a clubbing object. That doesn't work either. He heads back out to try to find something to get it, realizes the club in his hand is a gun (which was obvious the whole time), says "Come on, Dean!", and shoots the glass.
From the same episode, we have Dean tricking Sam into going back to the art exhibit so Sam can get together with Girl of the Week Sarah. Cue Sam suddenly noticing the haunted painting that he and Dean already destroyed, magically back again, and epically fumbling to recover from freaking out about it.
Sam: OH MY GOD!
Sarah: [startled] What?
Sam: The, that painting… [beat] … looks so good!
Meg's bitching and moaning over her demon brother shooting her with the fake Colt in "Salvation". "You shot me! I can't believe you just shot me!!" and "I'm so not in the mood for this. I've just been shot!"
And her reaction to John's snarky comments: "That was funny, John. I'm going to strip the skin from your bones, but that was funny."
Dean: For some reason I could really go for some pea soup.
Gallows humor at its finest, but the laugh's definitely needed as "Croatoan" is a pretty dark episode - the son of a woman infected by the Croatoan virus and killed asks where his mother is. Dean, the one who killed her, turns to Sam and mutters "Awkward..."
"Crossroad Blues" has Dean thinking MySpace is a porn site.
Sam and Dean are talking about Dean's now federal-level wanted status.
Sam: Dean, it's not funny. Makes the job harder, we've got to be more careful now.
Dean: What have they got on you?
Sam: [mumbling] I'm sure they just haven't posted it yet...
Dean: What, no accessory, nothing?
Sam: Shut up.
Dean: [laughs] You're jealous.
Sam: No, I'm not!
Dean: Uh-huh. All right. What do you got on the case there, you innocent, harmless young man, you?
Dean pretends to talk with a Crossroads Demon about making a deal to bring John back. He seems sold...
Crossroads Demon: Look. Your dad's supposed to be alive. You're supposed to be dead. So we'll just set things straight, put things back in their natural order. And you get ten extra years on top. That's a bonus.
Dean: You think you could... [he turns to face her] ... throw in a set of steak knives?
"Playthings" presents the rare and hilarious Drunk!Sam.
Sam:(petulantly) You're bossy.
Sam: (throws his hands out) You're bossy! (laughs) And short.
Dean: I never get to work jobs like this! Old school haunted houses; fog, secret passageways, sissy British accents... Might even run into Fred and Daphne... Mmmmmm, Daphne, love her.
Also, Dean lampshading the astounding amount of Angst in the show.
This conversation between Sam and Dean about angels in ‘’Houses of the Holy’’
Sam: Dean, there's ten times as much lore about angels as there is about anything else we've ever hunted.
Dean: You know what, there's a ton of lore on unicorns too. In fact, I hear that they ride on silver moonbeams, and that they shoot rainbows out of their ass!
Sam:(looking heartbroken) Wait, there's no such thing as unicorns?
While the point of that exchange is the unicorn bit the mention of angels becomes funnier in hindsight, as of Season 4.
And then Season 7 has a unicorn that does, in fact, shoot rainbows out of its ass.
When they discover the angel's "sign" was just an angel decoration, Dean concludes that the moral of the story is "Always take down your Christmas decorations after New Year's or you might get filleted by a hooker from God". Cue a very unamused response from Sam.
There's also something hilarious about the way he describes what hell is like, then says "Your dad was there to. He says HOWDY!"
It may be just me, but after Sam's exorcised (and keep in mind, Meg!Sam had just spent a few minutes punching Dean in the face while spewing a "The Reason You Suck" Speech):
Sam: ... did I miss anything?
Dean: ... (punches Sam in the side of the head)
Plus, Dean making the one observation at the end that gets the two chuckling after reflecting on the episode: "Dude, you like full-on had a girl inside you for like a whole week. That's- that's pretty naughty."
Fridge Hilarity sets in when you hear this episode referred to as the time Meg took her dad's car out for a joyride.
“Tall Tales” when the brothers are filling Bobby in, seeing them through the other's eyes. Sam. Is. Priceless.
And later that episode, Dean's reaction to some guy's fairly... traumatic alien abduction story is, 'So some alien made you his bitch?'
The victim then goes on to tell them the alien made him do something worse. When Dean asks what's worse, the show cuts to a shot of the tiny Roswell alien forcing the victim to slow-dance to "Lady In Red". Even better is the non-verbal reactions from our two leads. Especially Dean's.
Sam watching soap operas in "Heart".
All of the lampshading in "Hollywood Babylon":
Actress: I don't get it. Why would ghosts be afraid of salt?
Director: Yeah, I'm not sure about salt either. What else wards off ghosts, guys? Are we sticking with condiments?
Writer: How about shotguns?
Director: ... That makes even less sense than salt.
In "All Hell Breaks Loose, Part 1", Andy Gallagher, the funniest of the other Special Children makes a return. He mentioned that he got back at a jerk by beaming visions of gay porn into the guy's head.
Azazel coerces Jake into helping him fulfill his Evil Plan by unlocking the devil's gate. What unlocks it? The Colt. How does Azazel describe it to Jake, who is already pissed off and looking to kill him?
Azazel: Oh, this isn't just any gun, Jake. This is the only gun in the whole universe that can shoot me dead. (points Colt to his head)
‘’The Kids are Alright’’ Dean talking to Ben at the birthday party, and obviously doing the math. The pure 'oh shit' look on his face alone, not to mention Ben being an exaggerated mini Dean.
There's a lot of moments in "Bad Day at the Black Rock":
When the boys are looking at their kid stuff that their dad kept. Sam picks up his soccer trophy. Dean's reaction is, 'Yeah, closest you ever came to being a boy.' Then he picks up a gun. Which he made himself. In sixth grade.
Dean's response to Bela cutting him off mid-"You're no killer" speech (which had worked earlier on one of the other thieves) by shooting Sam in the shoulder.
Dean: What the hell is wrong with you?! You don't just go around shooting people like that!
Or how about Sam's pouty "I lost my shoe." Aww... and HEE!
Aw, hell. Everyone knows that it's not healthy to laugh at others' misfortunes, but anything that happens to Sam after the rabbit's foot is lost is freakin' hilarious.
[Samis sitting in a chair in the middle of the motel room, bored out of his skull. The air conditioner starts to rattle and then smoke.Samwatches in horror and disbelief.]
Sam: Aw, come on.... I didn't... I wasn't....
The air-conditioner promptly sets fire to itself. Sam puts it out with a sheet. The fire starts up again. He puts it out again. And again. And his sleeve somehow catches fire. He flails around, tangles himself up with the sheet and knocks himself out.
When Sam crashed to the ground trying to catch a stereo, taking a floor lamp with him. Dean's look of longsuffering is priceless.
Dean: Sam? Are you alright?
Sam: *from the floor* ...Yeah, I'm good...
Especially because he somehow manages to look like he's five years old at that moment, and it's freaking adorable.
Sam's expression after the blond vampire described a 30-year-old guy as "old" in "Fresh Blood".
The AMAZING moment from "A Very Supernatural Christmas" when the brothers are caught unprepared by the creepy mall santa they suspected of being a monster. The two, usually so adept at coming up with excuses and deceit have no idea what to do when the old man asks them what the hell they're doing in his home... until Dean starts awkwardly (and BADLY) caroling, soon joined by Sam as they scoot towards the door.
Before they go to take down the pagan gods that are this week's monsters, Dean is sharpening a stake, with a trash can sitting in front of him to catch the shavings. There's shavings literally all over the carpet around him, everywhere except the trash can.
The entirety of the scene with the assimilated pagan gods prepping a tied-up Dean and Sam for sacrifice is pretty damn hilarious.
Sam: So I guess we're dealing with Mr and Mrs. God. [beat] Nice to know.
In "Long-Distance Call", Dean gets a phone call from John, who is dead by this point in the story. He discusses it with Sam:
Dean: Okay, so what if—what if it really is Dad? What happens if he calls back?
Sam: What do you mean?
Dean: What do I say?
Sam: ... "Hello"?
Dean: (incredulous) "Hello"?
[Sam shrugs, looking uncomfortable.]
At the end of the episode, Dean admits that he was desperate for John to save him, but concludes that he can't expect anybody but himself to do it. Sam adds "And me".
Dean: "And me"?
Dean: Deep revelation, having a real moment here, that's what you come back with? "And me"?
Sam: Do you want a poem?
Dean: Moment's gone.
"Lazarus Rising" Dean discovering the modifications Sam made to his car and the two arguing like a pair of divorced parents about what their child should and should not be allowed to do.
Later, Dean and Pamela are flirting.
Dean: Dude, I am so in.
Sam: Yeah, she's gonna eat you alive.
Dean: Hey, I just got out of jail. Bring it.
Pamela: [passing by again, to Sam with a wink] You're invited too, grumpy.
Dean: You are NOT invited.
"In The Beginning" has this gem:
Dean: Sammy, wherever you are... Mom is a babe. I'm going to Hell. Again.
The introductory sequence of "Monster Movie," done as a black-and-white horror movie, complete with an ominous, Gothic sign reading, less than threateningly, "WELCOME TO PENNSYLVANIA."
That entire episode is a perfect parody of the old Universal monster movies, from the way it's shot to the music to the kissing scene to the monster himself (he's such a wonderful Large Ham).
The moment where Dean decides that the process of being returned from Hell has re-virgin-ized him.
Dean: Look at me, I came back from the furnace without any of my old scars, right? No bullet wounds, no knife cuts, none of the off-angle fingers from all the breaks. I mean, my hide is as smooth as a baby's bottom. Which leads me to conclude, sadly, that my virginity is intact.
Dean: I have been re-hymenated.
No one's gonna mention the lederhosen Dean wakes up wearing? Even Sam laughs at him!
Or the moment right after Sam rescues Dean when he tries to kick down what appears to be a thick, heavy door with iron hinges. Like everything else in the monster's home, though, it's really just a cheap prop. Sam gets his boot stuck in the panel he kicked and has to hop forward awkwardly on one foot as the door then slowly collapses away from him.
They decide to just open the next door they come to.
What about: "PUT ON THE GOWN!"
Or the bit with the pizza delivery guy?
"Dracula": Is there garlic on this pizza?
Pizza Guy: I don't know. Did you order garlic?
"Dracula": *looking horrified* Noo...
What about "Dracula" billowing away down a dark alley, springing over a high wrought-iron fence in one leap, and... motoring away on a Vespa?
Sam sneaking up on their suspect in a dark theatre, with the organ music said suspect is playing going from "creepy" to... um, "not creepy". Bonus points for Sam's eyeroll when this happens.
Dean (to the deputy): Know what? ...You're awesome.
Dean discovering that a vengeful trick-or-treater he brushed off earlier egged the Impala in "It's the Great Pumpkin, Sam Winchester," followed by his angry cry of "ASTRONAUT!" Made even more hilarious with Sam cracking up in the background.
Personal favorite: Teddy (hey, he signed his suicide note "T. Bear"), in the throes of an existential crisis:
Teddy: It is a terrible world. Why am I here?!
Audrey: For tea parties!
It's the tone that makes it clear she's already explained this repeatedly that kills me.
Dean's reaction to the bear. The guy can face down demons, vampires, shapeshifters and werewolves, but he is just not equipped to handle that. It only gets better when they talk about what they've just seen.
Sam: Are we... should we... [whispers to Dean]are we gonna kill this teddy bear?
Alastair: There's something caught in my throat. (beat) I think it's my throat.
"It's a Terrible Life": Dean driving a Prius while listening to NPR. Hell, Dean's entire day.
The Ghostfacers' instructional videos. "Winchesters still suck ass though." "Affirmative. Suckage: major."
How about Sam saying he'd broke up with his ex Madison but when he called her all he got was a Vet?
In "The Monster At the End of This Book," after finding out that Chuck is a prophet of God, Dean turns to Castiel and asks, regarding Chuck, "Seriously? Him? A prophet?" Cas' response? "You should've seen Luke."
Sam tells Dean aboutslash in the most hilarious meta moment ever.
When they're in the laundromat and Dean narrates Sam's actions.
Dean: "Sam turned his back on Dean, his face brooding and pensive." I mean, I don't know how he's doing it, but this guy is doing it. I can't see your face, but those are definitely your brooding and pensive shoulders.
Dean: (reading) You just thought I was a dick.
Sam: Guy's good.
Chuck and Dean bursting into the room to save Sam from Lilith:
Chuck: I am the Prophet ...Chuck!
The look on Dean's face when he tells Sam to "behave, don't do any homework, watch some porn" makes you think he's always wanted to say that sentence.
Castiel's Could Say It But to Dean, telling him to bring Chuck to the motel so the archangel watching over him will appear and destroy Lilith. The look on Cas's face is what turns it from simply awesome, into funny and awesome.
Dean then goes and tries to inspire Chuck into coming along with him. The music swells heroically... and then Chuck says "No frigging way!"
Dean: Okay, well then how about this. I've got a gun in my pocket, and if you don't come with me, I'll blow your brains out.
Chuck: I thought you said I was protected by an archangel.
Dean: Hm. Interesting exercise. Let's see who the quicker draw is.
In "The Rapture", while supposedly standing guard over Castiel's vessel Jimmy Novak, Sam slips out for a hit of demon blood, which Jimmy takes as his cue to sneak away. Dean seems to find the whole thing hilarious the next morning.
Sam: This is funny to you?
Dean: (around his toothbrush) Mr. Big Bad Prison Guard, Jimmy Mc Mook gives you the slip? Yeah, it's pretty funny. What were you doing anyway?
Sam: I was getting a Coke.
Dean: (pausing to remove the toothbrush, sarcastically) Was it a refreshing Coke?
In "Lucifer Rising," Dean sadly informs Bobby that he's so furious with Sam, he no longer considers him his brother; in response, Bobby launches into an unforgettable tirade:
Bobby: You stupid, stupid sonofabitch! Well, boo hoo! I'm so sorry your feelings are hurt, princess. Are you under the impression that family's supposed to make you feel good? Make you an apple pie, maybe? They're supposed to make you miserable! That's why they're family!
Castiel and Chuck's (temporary) Bolivian Army Ending versus a friggin' archangel. As their certain demise grows closer, Chuck reaches out and puts a hand on Cas' shoulder. Castiel responds by giving him a look and Chuck hastily removes it. Possibly made even funnier if you ascribe to the theory that Chuck is God in disguise, and was showing pride in his son for doing the right thing - and Cas doesn't know it and makes him stop.
In "Sympathy for the Devil", the boys enter John's lock-up to find two demons dead on the ground and a group of angels waiting in side.
Dean: [completely deadpan] Oh thank god, the angels are here.
Minutes later, they find out that Dean is Michael's vessel.
Dean: How? Why—why me?
Zachariah: Because you're chosen! It's a great honor, Dean.
Dean: Oh, yeah. Yeah, life as an angel condom. That's real fun. I think I'll pass, thanks.
Lucifer starts talking to his vessel:
Lucifer: I'm not your wife, Nick. I'm an angel.
Nick: An angel?
Lucifer: My name is Lucifer.
Nick: Sure. Naturally. Um… Could you do me a favor there, Satan, and remind me to quit drinking before I go to bed?
In "Good God, Y'all!": Castiel announces his intentions to find God and disappears. A crippled, wheelchair-bound Bobby shouts after him, "When you find God, tell him to send legs!" And before that, when Dean snarkiliciously tells Cas that he heard God was on a tortilla in New Mexico. Cas responds, in all seriousness, "God is not on any flatbread."
Castiel's adorably freaked-out expression when he goes with the prostitute in "Free To Be You And Me."
"Just out of curiosity, what is the average customer wait time to speak to an archangel?"
Raphael: [trapped in a ring of holy fire] Castiel, I'm warning you. Do not leave me here. I will find you.
Castiel: Maybe one day. But today, you're my little bitch. [leaves]
Dean: [turns to leave, pauses] What he said.
In "The End", talking to Dean on a mobile phone, he gets Dean's location and says he'll teleport right there. Dean points out he's in dire need of some sleep and says to come in four hours, and hangs up. Cut to Castiel standing on the side of the darkened highway, saying "I'll just... wait here then." And the shot stays on him, as he stands immobile, undoubtedly for the next four hours.
What makes this even funnier is that at the end of the episode, after he saves Dean from Zachariah, he's still standing there.
The faux Cosplay!Winchesters in "The Real Ghostbusters," especially when they reveal that they're a gay couple.
The Victim of the Week asks Chuck why Sam and Dean don't put their weapons on a bungee to keep them in hand. At the end, Dean (who had the fireplace poker knocked from his hand) says: "Maybe we should put these things on a bungee."
Becky letting Sam down lightly. With violin music.
The episode "Abandon All Hope" certainly lives up to its name, but the demon Crowley lightens the mood. After calmly handing the Colt back to the boys, asking them to go shoot Lucifer, Sam tries shooting Crowley, which doesn't work, as Crowley never reloaded it, then Crowley casually mentions that he should probably give the boys more ammo. Not to mention Crowley's "HOW ABOUT YOU DON'T MISS, OKAY?! MORONS!"
Castiel easing into slang.
The stand-out moment in "Sam, Interrupted" has to be when, caught in the morgue by the nurse, Dean drops his pants, wiggles his hips and gleefully shouts "Pudding!" to help him and Sam avoid suspicion or punishment.
Sam: So, the plan to kill me, would it actually stop Satan?
Dean: No! Sam, come on!
Castiel: ... No. She's... Glenn Close.
Since Castiel no longer has the powers of Heaven at his disposal, Time Travel is very difficult for him to manage, as shown when he arrives back in 2010. Dean and Sam hurry to hold him up and we get this:
Dean: Son of a bitch, you made it!
Castiel: [looking at himself in surprise] I did... [looks around at Sam and Dean] I'm very surprised. [keels over]
"I DON'T UNDERSTAND THAT REFERENCE."
The scene where Dean, Sam and Castiel meet a Cupid in "My Bloody Valentine." Particularly fascinating because that episode was quite hard to watch.
Sam: Dean, enough...
Sam: You just punched a cupid.
Dean: I punched a dick!
Bonus points because this is the second time Dean has punched a celestial being and he still hasn't learned that it's only going to hurt him.
How can you not mention that the Cupid was completely bucknaked during this entire scene? Apparently they always are, cause, like Cas said:
Castiel: They're not incontinent.
Then, before that:
Dean: Is this a fight? Are we in a fight?
Castiel: This is... their handshake.
Dean: I don't like it.
Castiel: Nobody likes it.
It's right around that moment where you can almost see Misha Collins breaking. His face kind of twitches and he's clearly seconds away from laughter. It's precious.
Castiel taking one for the team and his clumsy attempt to apologize to the Cupid for hurting his feelings. If you recall an earlier scene where Castiel picks up a human heart without hesitation, it makes that scene even funnier.
Castiel: Uh... look... we didn't mean to, um... (look to Sam and Dean for help; they wave for him to go on) ... hurt your feelings.
Cupid: (whirls and crushes Castiel in a tight hug, crying) Love is more than just a word to me, you know? I love love. I love it. And if that's wrong, I don't wanna be right!
Castiel: (awkwardly patting his back) Yes... yes... of course. I, uh... I have no idea what you're saying.
Later on, the trio is trying to figure out what to do:
Sam: So what, this entire town is just gonna eat, drink, and screw itself to death?
Castiel: [around a mouthful of hamburger] We should stop it.
Castiel: How did you stop the last horseman you met?
Dean: War got his mojo from this ring. And after we cut it off, he just tucked tail and ran. And everybody that was affected, it was like they woke up out of a dream. You think Famine's got a class ring, too?
Castiel: I know he does.
Dean: Well, okay. Let's track him down and get to chopping.
Castiel: Yeah. [eyes his empty fast food bad sadly]
Dean: What are you, the hamburglar?
Castiel: I've developed a taste for ground beef.
Dean: Well, have you even tried to stop it?
Castiel: I'm an angel; I can stop anytime I want.
More on Cas's OOC hunger:
Castiel:[bites into a fresh burger] These make me very happy.
Even though it comes right after a serious Nightmare Fuel scene and right before another, Cas and Dean's attempt to take out Famine has a funny moment in it.
Dean: You want to go over the plan again? [Cas doesn't reply, playing with the tinfoil from one of his burgers] Hey, happy meal. The plan?
Castiel: I take the knife, I go in, I cut off the ring hand of Famine, and I meet you back here in the parking lot.
Dean: Well, that sounds foolproof. [Castiel disappears][beat] This is taking too long. [goes in after him]
In "Dead Men Don't Wear Plaid," half a dozen dead people rise from their graves, including Bobby's late wife. Sam is tracking down the people who came back, the last being Ezra Jones. He finds her bedridden and looking like her skin is coming off. She's unintelligible, coughing constantly, and gesturing for him to come over. It's a tense moment, but Sam's comments make it hilarious.
Ezra: [coughs][beckons him over]
Sam: Any way you could tell me from here?
Ezra: [coughs harder][beckons more insistently]
Sam: [flatly] Yeah. I'm gonna regret this.
"Dark Side of the Moon": Zachariah to Dean and Sam: "Wow. Running from angels. On foot. In Heaven. With-out-of-the-box thinking like that, I'm surprised you boys haven't stopped the Apocalypse already."
Zachariah had a few in this one, from calling Mary a MILF to retorting to Dean's calling him bald with "in heaven I have six wings and four faces, one of which is a LION".
When the boys are about to make their run to the Garden.
The otherwise extremely unfunny "Point of No Return" had these jaw-dropping gems, which were hilarious purely for their inappropriateness:
Castiel: Maybe [the angels] are desperate. Maybe they wrongly assumed Dean would be brave enough to withstand them.
Dean:[annoyed] All right, you know what? Blow me, Cas.
Dean:[as Castiel watches him fixedly] Well, Cas, not for nothing, but the last person who looked at me like that... I got laid. [winks]
At the end of "Hammer of the Gods," Gabriel leaves a message for Sam and Dean to watch after his death... in the form of a pornographic film. After informing the boys about a few things, Gaberiel tells Dean that he was right; Gabriel was afraid to stand up to Lucifer. Ultimately culminating in the wonderful line, "This is me standing up. And this... is me lying down." And the porno resumes. With Gabriel still in the shot. Sam and Dean are incredibly Squicked out.
Although Dean KEEPS WATCHING until Sam closes the laptop.
Earlier in the same episode, even before Gabriel gets his Crowning Moment of Awesome for breaking "Lucy"'s Smug Snake facade, he gets one of the best lines of a non-Castiel angel in saying "Lucifer, you're my brother, and I love you, but you are a great big bag of dicks."
The moment Gabriel walked into the room earlier in the episode, the other gods calling him Loki and saying in his usual devil-may-care manner, "We need to talk about the elephant in the room. *Ganesh starts to stand up angrily* Not you, big guy."
"The Devil You Know," anyone? Crowley suddenly appearing in the back of the Impala. Sam trying to shiv Crowley repeatedly. Crowley complaining to Sam and Dean: "THEY ATE MY TAILOR!" and "Here I am standin' in the middle of the road, talkin' to Sam and Dean Winchester UNDER A FRIGGIN' SPOTLIGHT!" And proceeds to telekinetically shoot out a streetlight.
Crowley: Not that one. [pats his Hellhound which is roughly five feet tall] I brought my own. Mine's bigger. Sic 'im, boy!
Crowley's innocent look at Dean like "What did I do?" after beating the demon's skull for awhile.
Brady panicking during the hellhound attack and no one caring:
Brady: Damn it, get me out of here!
Sam & Dean: (in unison) Shut up!
In ‘’Two Minutes to Midnight’’ Crowley continues to entertain us when the boys learn that Bobby made a deal with him. He took a picture to prove than they kissed when they made the deal. Bobby is not pleased.
Bobby:Why'd you take a picture?
Crowley:Why'd you use tongue?
He pulls about a half-dozen vanishing acts on Dean in the course of a minute. It's Hilariawsome.
Before Crowley shows up there is this little exchange.
And Castiel makes a Big Damn Heroes entrance to save Sam & Dean from Pestilence:
Pestilence: How did you get here?!
Castiel [panting]: I took a bus.
Dean: Don't worry, Bobby's here, he'll wire you some cash.
Bobby: I will?
Or how about Cas's apology to Dean for his doubts:
Castiel: You are not the burnt and broken shell of the man that I believed you to be.
Dean [flatly]: Thank you. [pause] I appreciate that.
Castiel [sincerely]: You're welcome.
Dean winds up having pizza with Death. It's easy to miss with how terrified Dean is, but when Death instructs him to eat the pizza and asks him if it's good, there's a brief moment where Dean silently acknowledges that yeah, it is pretty good.
Castiel calling the Archangel Michael (/his older brother) "assbutt".
And Dean's reaction:
Dean [in dismayed disbelief]: "Assbutt"?
Castiel's last-episode discovery of Dean Winchester's favorite maneuver, the bald-faced lie.
Lucifer: (rhetorically) Castiel, did you just molotov my brother [Michael] with holy fire?
Castiel: (smiling awkwardly, knowing perfectly well that Lucifer saw the whole thing) Um... no?
Earlier in the episode, Dean injecting his normal snark into a heartwarming moment.
Dean: It's not on me to let you do anything. You're a grown — well, overgrown — man.
Exile on Main St:
Dean: It's... it's a sport!
"The Third Man" had some great Castiel lines.
From his serious business, deadpanned, unfunny self:
Castiel: The weapon isn’t being used at full capacity. I think we can rule Moses out as a suspect.
Explaining why he answered Dean's prayers and not Sam's:
Sam: So, what, you like him better or something?
Castiel: Dean and I do share a more profound bond. [[to Dean]] I wasn't going to mention it....
On why Sam and Dean should help him, even though he's been ignoring them:
Castiel: (with air-quotes) Sam. Dean. My "people skills" are "rusty". Pardon me, but I have spent the last "year" as a multi-dimensional wavelength of Celestial intent.
Dean trying to slow Cas down long enough to explain what's going on:
Dean: There’s too many angels, Cas. I don’t know who’s on first, what’s on second?
Castiel: What is second?
Dean: Don't start that.
Cas and another angel fall out a fourth-story window and land on Sam's car, totaling it.
In Family Matters, Castiel makes a Call Back to one of Zachariah's quotes about what they actually look like in heaven, when he says (regarding Jimmy's being scrawny): "This is… a vessel. My true form is approximately the size of your Chrysler Building."
"Clap Your Hands If You Believe..." had some gems:
When Dean is telling Sam over the phone he is currently being chased by aliens, a close encounter of the third kind, desouled!Sam replies "Better run, Dean. I think fourth kind's a butt thing."
When Dean actually gets abducted, Sam is relating the tale and mentions that he's gotten adjusted to it. Someone says that it must have happened when they were kids, to which Sam replies: "No, half an hour ago".
Dean's description of his abduction:
Dean: "There were these… beings, they were too bright to look at but I could feel them pulling me towards this sort of… table."
Sam is getting his ass handed to him by a leprechaun, but is able to stop him by spilling salt, which leprechauns must count. He even lampshades that he waited before doing it by saying "Why didn't I try this earlier?" As he's finishing the spell to send every Monster of the Week back to whence it came, the leperchaun, still counting, goes "...three... (looks up) you ass."
In jail for assaulting a dwarf while, as mentioned above, yelling about fairies, a cop questions Dean as to the reasoning behind his crime.
Officer: I'm just trying to understand just what kinda hate crime this even was.
Dean: It wasn't a hate crime.
Officer: I mean, if this gentleman were a full-sized homosexual, would that be okay with you?
In one season 6 episode, Dean is trying find Sam. When asking if someone had seen him, he says "he's about 'yea high'", and motions as high as he could possibly reach. It should be noted that the difference between Ginormo (Sam) and 'Lil Stumpy (Dean) is 3 inches: 6'4 and 6'1.
Castiel watching porn in "Caged Heat". "If the pizza man truly loves the babysitter, then why does he keep hitting her rear? Perhaps she's done something wrong?"
Dean scolding Cas for watching porn in the same room as him and talking about it, Cas looking toward his crotch with a confused expression, and Dean's exasperated "Great, now he has a boner."
Samuel: Is this what you boys do, sit around watching pornos with angels?"
Castiel: We're not supposed to talk about it.
And after his Foe Yay moment with Meg, Cas says, "I learned that from the pizza man." Who says porn isn't educational?
Also funny is Meg's reaction; "A+ for you! I feel so clean…"
The middle-man demon handling the alpha-exchanges between Winchesters and Crowley: "I'm sorry, I know you're speaking, I see your lips moving, but I can't understand what you're saying 'cuz I don't speak little bitch."
"Apointment in Samarra": Dean has to be a reaper for a day. He harvests the soul of a heart attack victim. "Why?" "Probably the extra cheese"
And earlier, when a guy who got shot while trying to rob a convenience store asks the same question, Dean replies with, "Mostly because you're a dick."
In the same episode, Sam corners Bobby in a closet and takes down the door with an ax. Bobby's response?
Any scene with Death is quite often this, as he is ironically something of a Deadpan Snarker. Special mention goes to ‘'Appointment in Samarra'’, where he runs rings around Dean when negotiating getting Sam's soul out of Hell. When he challenges Dean to wear his ring and be Death for a day, and asked if he's serious: 'No, I'm being incredibly sarcastic.'
Castiel and Sam's reunion in ‘’Like a Virgin’’, after Sam gets his soul back and loses his memory (the tone of Misha Collins' voice just sells it):
Sam: Um, look I would hug you, but…
Cas: That would be awkward.
This conversation from earlier in the same episode:
Sam: So what kind of thing likes virgins and gold?
From the same episode: Dean trying to pull the sword out of the stone and failing. Twice. And how he thought resorting to explosives would end well. Naturally, it broke the sword.
Dean trying to pull the sword out of the stone while the world's most heroic music plays in the background which fails spectacularly when he doesn't manage to pull it out. WARNING: do not watch this video while drinking or extreme spit-take will occur!!
In "The French Mistake", when Virgil is shooting up the set, Serge Ladouceur, Supernatural director of photography (though played by an actor here), casually bends backwards to dodge a bullet with a look on his face that says neither "Everyone around me is dead" nor "I'm about to die." He then exits stage left.
Early in the episode, as Sam and Dean are getting their bearings, we have this exchange:
Sam: Well, I mean, here, wherever this is, this "The Twilight Zone" Balthazar zapped us into, for whatever reason… our life is a TV show.
No one else found Castiel in a cardigan even a little giggle-worthy?
Sam does some research on who Jensen Ackles is… and finds a Youtube clip of his time on Days of Our Lives.
Dean: *quickly slamming the laptop shut* "I do not like this universe. We've got to get out of this universe."
Sam and Dean go to Jared Padalecki's house… and meet his wife Genevieve, aka Ruby. Their reactions are hysterical, especially when she walks out of the room and both brothers blatantly check out her ass.
Following Sam and Dean being spotted laying the smackdown on a depowered Virgil, the crew are seen in a conference call to executive producer Sera Gamble.
Robert Singer: Well, Sera, it appears Jared and Jensen were seen... beating an extra to death.
Let's face it, 'The French Mistake' is a Crowing Episode of Funny, from the casual acceptance of the crew to Sam and Dean playing Jared and Jensen as "*sigh* Season six…" to their reactions when they learn Sam married New Ruby to Sam and Dean reacting to Executive Producer Bob Singer having named Bobby after himself.
Special mention has to go to Eric Kripke getting shot to death by Virgil, and Robert Singer screaming "NOOOOO!" in slow-mo.
"The French Mistake", along with being what is probably the funniest episode in the series, was one Fandom Nod after another. It gets even funnier when you realize that the episode's title is a Shout-Out to Blazing Saddles. In particular, a really Meta scene where the fourth wall gets trampled. It's even better when you realize that the scene is a musical reference to gay sex. It's a massive blending of Fandom Nod and the Running Gag of Sam and Dean being Mistaken for Gay.
Sam and Dean beating the crap out of a powerless Virgil. It's the incredibly malicious grins on their faces when they realize that they finally have the upper-hand on an angel that really gets to her. When crew-members intervene:
Dean, while trying to break free and go kick his ass some more: YOU'RE A DEAD MAN, VIRGIL!
Sam, also struggling: DIE!!
[Virgil runs away]
In "And The There Were None", when Bobby asks Rufus how long he's had a pacemaker:
"Since Bush Junior term one. I'm also short three toes, FYI."
In "My Heart Will Go On", when Balthazar is explaining to Alternate!Sam and Dean why he changed history by stopping the Titanic from sinking:
And then there was this moment when Balthazar tried to stab Atropos, only for Cas to stop him in time. He grins sheepishly. "Awkward!"
Earlier in the episode, after one victim gets hit by a bus after turning down the boys' efforts to help him, Dean points out the irony of the bus having one of the guy's business ads.
(Sam gives Dean a look)
Dean: …Too soon?
Sam: Yeah, dude, six seconds is too soon.
"Frontierland" has plenty, mostly from Dean's Wrong Genre Savvyness while in the past (to clarify, no one in the Old West acts the way Dean's seen them do in the movies, so they tend to look at him like he's crazy).
Sam and Dean geeking out over Samuel Colt's journal.
"I'm the posse magnet. …I love posse."
Not to mention Samuel Colt describing Sam as "a giant from the future with a magic brick."
Once they find where (or rather, when) to get ahold of a phoenix, Dean calls Castiel, knowing he's the only one who can zap them back to the past.
"Mommy Dearest" has plenty, before the Mood Whiplash sets in. First, when Dean is complaining about how he's the one who always has to call Castiel for help - "It's not like he lives in my ass!" - the camera cuts to show Cas standing right behind him:
Dean: (startled) Cas!... Get out of my ass!
Castiel: (confused) I was never in..your... (trails off)
Later, when the group is in a cafe and trying to find information on any local weirdness, Bobby is having some trouble with an iPad:
Bobby: I said I needed a computer.
Sam: That is a computer.
Bobby: A computer has buttons.
Then, when Castiel finds that he can't teleport and tries to focus (think Hiro), Dean comments that he looks like he's "trying to poop".
Castiel sulking after Dean tells him while he's powerless he's as useful as a "baby in a trenchcoat." Sam gives Dean a look and discreetly whispers "You hurt his feelings."
And a little while after that, when the two go the local doctor's office to try and get information from him:
Dean: Hey, is the doctor in? My friend's got a problem.
Castiel: I have a… painful burning sensation.
Assistant: Sorry, he's out. (to Cas) I suggest some ointment.
When they discover Eve's hybrid monsters, Dean decides to name them "Jefferson Starships", because "They're horrible, and hard to kill."
And insisting on the name.
"The Man Who Would Be King" opens with Castiel reminiscing on some things he's seen over the ages, including the Tower of Babel:
"Thirty-seven feet, which I suppose was impressive in those days. And when it fell, they screamed 'Divine Wrath!', but come on. Dried dung can only be stacked so high."
Cas also shows that he's finally grasped the concept of cursing, during a flashback that shows his first dealing with Crowley:
"I'm an angel, you ass."
And later on in the episode, another flashback shows what Crowley did to Hell after taking over — he turned it into an endless waiting line. And when you finally reach the end of the line, you just start over. Crowley justifies this by saying that this is a much better form of torture than what was there before.
"A lot of people who were coming here were masochists anyway, a lot of 'thank you sir, may I have another hot poker shoved up my jackery?' But nobody likes waiting in line."
In "Let It Bleed", Dean explains to Sam and Bobby why he's never read H. P. Lovecraft:
Dean: I was busy having sex with women.
I love how he has to specify "women."
And later in the episode, someone describes Castiel by saying he "looks like Columbo and talks like Rainman."
And when Balthazar decides to side with the boys.
Balthazar: Because - I know I'm gonna live to regret this - but I'm officially on your team. [Beat] You bastards.
The Season 7 premiere "Meet the New Boss" had quite a few gems, specifically the whole scene with Death, from his exchange with Castiel to his calmly eating his meal while the Winchesters and Bobby just stand silently.
Basically all of Lucifer's scenes in the first two episodes (especially "Hello Cruel World"), from him playing golf with a fireplace poker to appearing in Bobby's living room reading a trashy newspaper.
Lucifer: You know, I think Prince William has really found the right girl.
Dean punching Sam right in the face the minute he opens the door.
"Defending Your Life": Sam defeated Osiris by running him through with a shofar of all things.
This is after the rabbi walked in on his stealing the horn. No, Sam was not at the temple for bar mitzvah lessons.
The brothers "counseling" the Starks in "Shut Up, Dr Phil", which mostly consists of Don and Maggie shouting at each other while flinging the brothers (especially Dean) around the room every time they interrupt. It ends with the couple making out while Dean is pinned to the wall with a swarm of hornets in his face.
"Slash Fiction": The Leviathan clones of Sam and Dean comparing notes on the brothers, complaining about all their issues. It concludes with Leviathan!Sam offering to switch bodies with Leviathan!Dean, only for Leviathan!Dean to turn him down because "I like this one's hair better."
Leviathan!Sam: I had a brother with this many issues once. Know what I did?
Leviathan!Sam: I ate him.
There's also the brothers' interactions with Frank, especially when he smashes Sam's laptop, then calmly hands him a new one and demands $5000 cash in payment for it. Also, Dean's reaction when told to ditch the Impala.
Dean silently singing along with Air Supply and totally getting into it. And Sam's reaction to it.
Props to Jared for staying in character the whole time.
The sheer audacity of Dick Roman telling off an obviously shocked Crowley for thinking thinking they could work together and calling demons "ugly, lazy, gold-digging whores." Crowley's reaction is to let Dick keep the baby uvula muffins and vamoose. 'Bout time that guy got an ass-kickin'.
Ness: Look, you seem like a swell guy, Lester, and I want to help you out, I do, but my partner here? He just back from the war. And he's spent the last two years kicking in Nazi skulls. If he doesn't kick in a skull every couple days, he gets real touchy.
Sam: What, are you gonna look at more anime or are you strictly into Dick now?
"Plucky Pennywhistle's Magic Menagerie": Episode opens similarly to "Yellow Fever" with Sam fleeing in terror from a deadly clown, only to flashback 60 hours earlier. As the episode catches up to the "present", we return to Sam's fleeing with the timeline subtitle: RIGHT FRIGGIN' NOW
Say what you will, but there's something deeply hilarious in watching solid badass Sam get his ass utterly handed to him by a pair of clowns.
Also, in a nice Call Back to "Houses of the Holy", after the second victim is killed by a unicorn, it runs off with a rainbow clearly coming out of its ass.
Is it too late to say that Howard summoned a couple of gay clowns?
This line when the brothers suspect something's up with the daughter.
Dean: Can you get to her without tripping the AMBER Alert?
You can practically see Dean's pupils dilate at the sight of the giant slinky.
Dean's description of the ways people are dying.
Dean: Seriously. Dractopus, Seabiscut the Impaler, Land Shark, what's next…
And then Sam being sent to look after someone they think will be the next victim.
Sam: Dude, one of them sprayed me with seltzer from his flower.
The terrified look on Sam's face the entire time he's investigating "Plucky Pennywhistle's Magical Menagerie"?
Right after Dean manages to end the magic that's keeping the clowns that are beating the crap out of Sam around, they burst into glitter as they're about to tackle Sam. Episodes like this are a great reason to watch the show, because you will never see such a giant man covered in so much glitter with such a look of utter terror on his face anywhere else.
"Repo Man": Schizo!Lucifer is back to pestering Sam like he had been at the beginning of the season. At one point, a library full of people start to slam their heads against their desks. Sam presses into his palm, revealing that it was all an illusion, and Lucifer pouts.
Lucifer: Come on, Sam! Pay attention to me, I'm bored!
Earlier on there's Lucifer sticking out his tongue at Sam. It's forked.
And then there's the serial killer and the demon slow dancing, and Dean's reaction.
The demon's Roaring Rampage of Revenge against the brothers (for causing him to sell Lilith out and get black-listed in Hell for eternity) is cut abruptly, hilariously short when he accidentally walks right into a devil's trap that appeared out of nowhere. The demon himself can't believe his rotten luck. ("You've got to be kidding me!")
From "Out with the Old," the cursed vintage gentlemen's magazines, and both brothers asking how the magazines can kill people before changing their minds.
While Sam is telling Dean how Lucifer's slowly driving him insane:
Sam: He's singing Stairway to Heaven. Dean: Good song. Sam: Not fifty times in a row.
The way Joyce threatens and intimidates George in a nonchalant way, starting with her telling him she's killed her past four assistants and keeps on. Makes it all the more satisfying when her head is cut off and George reveals his intentions to eat her.
Lucifer driving Sam crazy in "The Born-Again Identity" is kinda Black Comedy by using a megaphone.
Lucifer's antics with Sam in the mental hospital are all a special kind of black comedy; amongst said antics are chucking cherry bombs at his bed, turning his food into insects ("So, what'll it be today? Maggots or tapeworms?"), singing incessantly, and the aforementioned megaphone.
When Meg and Dean are trying to reassure Castiel that he knows how to smite demons, we get this:
Castiel: But I don't remember how [to smite demons].
Dean: It's in there. I'm sure it's just like riding a bike.
Bonus points for this not being the first time Garth's actor has pulled an Unflinching Walk away from something burning to a worrying height. On the other hand, DJ Qualls wasn't quite so unflinching the last time.
That funky background music playing whenever Garth shows up makes me smile.
Garth just lightens the mood in general, it's hard to stay mad at him. He really does grow on you.
The anticlimactic blessing of the samurai sword. A Shinto priest was unavailable, so Dean substitutes with a local sushi chef.
When the sushi chef mentions it's better to do this in a running spring, Dean pulls out a bottle of spring water to pour over the sword.
At the end of the episode, Bobby's return as a ghost and his annoyed reaction to Dean not noticing him when he goes back to get his flask from his motel room. Also counts as both a Tearjerker and Crowning Moment of Heartwarming
Dean: There you are. (picks up flask from table)
Bobby: I'm right here, ya idjit!!!
The use of Walking on Sunshine from "The Girl with The Dungeons and Dragons Tattoo". Then again Charlie in general.
Dean instructing her step-by-step on how to flirt with a man and Sam's barely contained laughter at it. He's hilariously good at it too.
Dean: (to Sam) This never happened.
Charlie: I feel dirty.
Dean: You and me both, sister.
"Reading is Fundamental" has plenty of these, including Castiel's crazy new persona (though this is also extremely tragic, all things considered).
Kevin: Are you one of the angels?
Castiel: (pokes Kevin's nose) Boop.
Plus his obvious attraction for Meg (including haven written her a poem) and of course, almost all of nerdy but adorable Kevin's lines and actions, and the reaction of the other characters to him, including:
His attempt to steal the Word of God tablet from Sam and Meg, with him desperately screaming and begging them to leave him alone as Sam runs after him.
Meg: (to Kevin after she tackles him) You're not a demon or a chomper, what the hell are you?
Kevin: Kevin Tran, I'm in Advanced Placement. P-p-p-please don't kill me.
And when Dean sees him curled up and screaming over seeing three angels being banished:
"Survival of the Fittest" has more of crazy!Cas ("How important is lipstick to you, Dean?"), especially Crowley's reaction to him. Made even better by the looks on Sam and Dean's faces, which basically scream "Just go with it."
"Are you off your rocker? Is he off his rocker? Is that what this is?"
There's something funny about seeing Crowley and Dick working out the details of the contract representing their deal.
Crowley: I suppose you want it in writing.
Dick: I don't kiss on the mouth.
Crowley: Your loss.
Apparently the Winchesters tried calling Cas and he showed up on top of the Impala, clothed solely in bees.
"We Need To Talk About Kevin" has the title character's drunken message on Sam's voicemail.
"Sam, I don't know if you're still alive. But if you are… EAT ME!"
And Dean replays that part just to prove a point.
Dean's joy at his first burger since he got out of Purgatory.
Dean's dull reaction to Sam's Technobabble explanation for how he's backtracked Kevin's location, and then asking for it in English.
Kevin asks where the brothers have been for the past year. Dean's response:
"Cliff notes: I was in Purgatory and Sam hit a dog."
Kevin tricks Crowley and as Kevin is making his escape we see Crowley standing in the middle of a field surrounded by goats.
When Kevin finally gets a chance to speak with his girlfriend, he apologetically tells her that she is being possessed by a demon and she's attending her safe school.
That last part is what causes her to give an outraged "What!?"
"What's Up Tiger Mommy" has Sam and Dean's nonchalant conversation while Kevin and his mother get anti-demon tattoos five feet away.
The funnier thing is that Kevin is screaming like a baby, while his mother is merely sitting there stoically while holding his hand through it all.
And her earlier nonchalance at getting a tattoo, saying she's done it before. Kevin is stunned.
Mrs. Tran punching Crowley is both this and an Awesome Moment.
Sam, Dean, Kevin, and Mrs. Tran pool their money (about $2,000, a bunch of hacked credit cards, and a Costco membership card) in the hopes of having enough to buy the tablet, only to have a hilarious Oh Crap when they realize that the auction doesn't use conventional money.
That said, the angel Samandriel and Crowley's competing bids:
Crowley: You think someone named "Buzz" gets into space without making a deal?
Made even funnier when you've seen Mark Sheppard on Doctor Who and given what happens in the episodes he's in.
Afterwards, when Mrs. Tran bids her soul for the tablet, Crowley is told that he can't offer more souls because offering up your own soul makes it more valuable. So Crowley tries to bid his own soul… only to be laughed off and told that he doesn't have a soul.
The college students in "Bitten" assuming that Sam and Dean (who they think are FBI agents) have a "workplace romance".
Kate saying that Sam and Dean can't be FBI agents because FBI agents "don't say 'awesome' that much." Becomes a Brick Joke at the end of the episode:
He also claims to have killed the Tooth Fairy, which he deeply regrets having been forced to do.
When Garth's asking about how Dean got out of Purgatory, Dean deflects the question by asking about the decor of the bar they're in. Garth then goes into a Civil War history lesson that leaves Sam and Dean rather surprised. When asked how he knows so much;
Garth: Civil War Reenactments, once a year, every year.
"A Little Slice of Kevin" has a small moment where Castiel comments on how he "missed television". Bonus points for sitting there watching one while Sam and Dean are in the middle of investigating a case.
When Castiel explains that there can only be one prophet at a time, Sam asks how Kevin can be one then if Chuck is around. Castiel's response:
Mrs Tran constantly spraying anyone who enters her and Kevin's hideout with holy water. Especially Kevin's exasperation at it.
Speaking of Mrs T, her annoyance when Sam hand cuffs her to her car's wheel to make sure she doesn't interfere when they go rescue Kevin.
Some of the potential prophets think that Crowley's an alien who's abducted them. He, at least, finds it hilarious.
This is even more Hilarious in Hindsight when you consider the fact that Crowley's actor, Mark Sheppard, has been on Doctor Who (granted, as a human agent and not an alien, but still). As Tumblr eloquently put it: "Right actor, wrong show."
Also, one of the potential prophets tries to bluff read the tablet... by quoting the Declaration of Independence.
Mrs Tran found a witch on Craigslist.
After Dean sees Castiel for the first time only for him to disappear, he's stunned. Sam has this to see upon seeing the look on his face:
"You okay? You look like... well, I was gonna say you look like you'd seen a ghost, but you'd probably be stoked."
It's easy to miss amongst all the major plot points being tossed around, but if you look at Cas when he gets zapped to Heaven temporarily that his tie is on backwards.
Addendum - his tie apparently is always on backwards.
The pure, unadulterated, Adorkable glory that is "Hunter Cas" in "Hunteri Heroici". Between his earnest attempts to fit in with the Winchesters (including his irritation over not being allowed in the front seat of the Impala) his use of his angelic powers to sniff the corpse of the episode's first victim to discover he had a bladder infection, his attempt to play Bad Cop to the victim's wife, his attempt to interrogate a cat (again playing Bad Cop), and many other examples, he was simply epic in this episode.
The episode itself was hilarious with it's use of cartoon physics being responsible for the episode's deaths, i.e. someone's heart beating out of their chest when they are in love, someone hanging midair a few seconds before they look down and plummet, someone being killed with a huge anvil in a bank robbery. The best example has to be Dean's "cartoon fight" with the episode's villain.
During the fight, there's a Road Runner/Wile E. Coyote gag with Dean and the villains' latin (or scientific) names.
"Torn and Frayed": Dean's exasperation at waking up to find Castiel standing over him staring at him.
Dean trying to hide the Asian porn on his laptop from Cas.
When a burn victim asks Dean whether he's serious when asked to remember the exact Enhocian words he heard earlier, Cas says "Yes, that's his serious face."
"LARP and the Real Girl": The ending, namely Dean leading the LARPer troops into a battle, complete with Rousing Speech taken directly from Braveheart. There's dramatic music too, which pauses when they need to stop because someone threw a frisbee into the middle of the battleground.
Charlie: Is that the speech from-
Sam: It's the only one he knows.
Earlier, when Sam announces that one of the victims had been killed by belladonna poisoning, Dean and Charlie simultaneously exclaim, "The porn star?!" Cue stare from Sam and awkward silence…
Dean getting fed up with the geeks, pulling out his gun and firing it off, causing everyone to jump.
Everyone except Sam. Who seems all too used to (and tired of) Dean's antics.
Dean repeatedly wandering off-topic to help Charlie improve her tactics in the LARP and getting into the game.
"Everybody Hates Hitler": The title.
Aaron's reaction to the body burning: "Oh God. These guys are psychopaths…"
Aaron: When I went to high school I sort of... drifted. I started getting off the academic track, and, uh, I kind of... ... I kind of smoked it.
"Trial and Error":
Dean on his decorating his room in the Men of Letters hideout: "I'm nesting."
Dean's comment on his bed: "It's Memory Foam. It remembers me."
And then literally moments after he mentions how much he likes having a clean room, Sam tosses a gum wrapper and misses the trash can. The look Dean gives him is priceless.
When Dean gets a call from Kevin about his breakthrough on the tablet, he ditches his (apparently fantastic) burger to make for Kevin's safe-house-boat. Sam gets up to follow...and then comes back for his burger.
Dean on seeing his digs at the Cassidy house: "I miss my room."
Dean, to a horse, after mucking out some stalls: "I hate you."
In "Man's Best Friend With Benefits", there's the way that Sam falls back and lands in the bin after being forced back. It's as though Jared was aiming to fall normally, landed with his knee stuck and then just carried on with the scene.
Sam congratulating Dean on his personal growth, having gone for over 15 hours without making a bestiality joke.
Portia noticing Dean's obvious distraction trying to work out the logistics of James and Portia's sex-life, clearly wondering if "Doggy-style" might be literal in this case?
Sam tries to prevent Dean from throwing out Dog!Portia, trying to get him to let her stay the night so they can find her owner in the morning (thinking at the time she's just a regular Doberman). Then Dean sees Human!Portia:
Dean: [looks in at her lounging on his bed] She can stay the night.
Sam: [sees Portia as a human] Two seconds ago she was a dog.
"Remember the Titans"
"Shane's" former flame showing up with a son who shares his curse. They explain everything to her.
Hayley: Okay, so Ollie's dad is a Greek God who has been cursed to die every day by Zeus. And you guys are...Ghostbusters. Am I getting this right?
Dean: Well, you know, due to the fact that your son is currently, albeit temporarily, dead, I'm gonna let that one slide.
Dean's failed attemped at humor with "Dragon Penis"
Dean starts planing a robbery to get an ingredient - a fulgurite - only to be told by Hailey that the stone in question can be bought cheap at new age shops.
And he looks so disappointed, too.
Even more Hilarious in Hindsight when you remember in Season Seven that they robbed a couple of a fulgurite to summon Death.
When they're trying to figure out who "Shane" is:
Sam: What do we know of that has Jason Bourne fighting skills, dies a lot, and has a history with violent women?
Dean finding the very first edition of Busty Asian Beauties (titled "Voluptuous Asian Lovelies") in the bunker, admitting that he does know how it would sell for on eBay, before finally asking Sam for ten minutes.
Meg: No, I get it. You met a unicorn and you fell in love. It was happy, then it was sad. I laughed, I cried, I threw up a little in my mouth.
Crowley finds out that Cas is the one who's been screwing up his operations, bringing either a bit of corpsing or Actually Pretty Funny from Sam.
Crowley: Castiel. So, that's who's been poking my boys — and not in a sexy way.
When Crowley proposes a deal with Naomi, she leaves silently before he even finishes.
Crowley: Maybe we can make a deal before this gets truly bollocksed. I mean, I must have something that you want. [looks over, notices she's gone] Tart stole my move.
"Freaks and Geeks"
Dean asks to speak for a moment with the boy who has been flirting with Krissy all episode.
Dean: Aiden. Listen, there's, uh, something I want to tell you about Krissy.
Aiden: I know. I know. You'll kill me if I ever hurt her. Blah. Blah. Blah.
Dean: No, no. No. She'll kill you. [pats him on the back] Good luck.
"Taxi Driver". Sam finds Bobby in Hell. Bobby immediately punches him in the face, assuming it's just another demon trying to torture him. Sam then proceeds with one of the weirdest examples of a Trust Password ever seen.
Sam: If it's not Sam... Then how do I know all about you and Tori Spelling?
Sam: You're a fan. Yeah. Or — or, uh... Okay. What about your free pedicure at the Mall of America? You made Dean swear to never tell another living soul how it changed your life.
When the two are making their way back into Purgatory, a doppleganger of Sam tries to confuse Bobby. Bobby stabs one, getting the demon impersonator.
Later, they're trying to nail down what the Monster of the Week is, and Charlie keeps shooting down Sam's suggestions, having eliminated the possibilities on her iPad:
Sam: [glares at the device] I hate that thing. [beat] I want one.
After Charlie is attacked by a djinn, Dean drinks dreamroot to help snap her out of the coma she's stuck in.
Dean: [to Sam] Alright, I'm gonna need to go sleep fast, so, punch me. [SAM gives him a look] Look, man, I know you don't want to, okay— [gets punched by Sam, but not knocked out][beat] Well, you're a little off your game there, cause I was— that was pretty— [Sam cold-clocks him]
"The Great Escapist"
Crowley asks Kevin just what it was that made him realise the Sam and Dean checking up on him were Crowley's fakes.
Kevin: Really, it was the way they acted. I don’t think on their best day Sam and Dean would go into town and get me a barbecue dinner. Not when there are leftover burritos in the fridge.
[Crowley pulls a scroll that he throws out to unroll in the remaining 10 feet between him and the brothers. Dean looks down at the enormous contract.]
Dean: Yeah, I'm sure there's no hidden agendas in there.
Sam is about to go into confession. Problem is he doesn't know where to start. Dean suggests a few of Sam's finer moments (Ruby, killing Lilith, setting Lucifer free, losing his soul, not looking for Dean when he was in Purgatory), and then:
When Castiel tries to use his angel powers on what looks to be a biker dude at a payphone. They don't work and the guy's reaction is "I'm gonna finish this phone call and then I'm gonna stab you."
Castiel repeatedly insisting that he doesn't need food or water. Later at the a laundromat (after he's stripped off his bloody clothing to wash), he has to choose between using the money he has left to either wash the clothes or buy a snack. He leaves with the most ridiculous clothes on.
Dean has Crowley in the Impala's trunk: "One for yes, two for no. You alive?"
When Dean is confronted by an angel and another one, named Ezekiel, approaches and the two engage in a fight before Dean kills the one who attacked him. Ezekiel tells Dean he has come to help...before passing out. Dean frowns and mouths "Okay." with the most hilarious expression.
"Devil May Care":
Dean's advice to Kevin. "Oh, next time the world's ending, grab a gun!"
Dean and Abaddon. "Are we gonna fight or make out bitch? Because I'm getting mixed signals."
Crowley's entire conversation with Dean and Sam, with this highlight. "Torture? Great, can't wait to see Sam in stilettos and a leather bustier. Really putting the S-A-M in S And M." And "What are you going to do to me that I don't do to myself for kicks, every Friday night."
Sam mentions that the area they're in might still be poisonous. Dean covers his junk.
Crowley: You'll connect me to Abaddon right away or I'll be forced to-[beat]
Sam: What? What happened?
Crowley: I've been placed on hold.
When Crowley refuses to help Sam translate the tablet, Sam mocks Crowley by saying that Abaddon is scarier than he's been in years. The King of Hell retaliates by crumpling up a piece of paper and throwing it in Sam's face like a pouty little kid. Crowley really showed him, huh?
"Rock and a Hard Place":
Not long after the boys take a purity pledge, becoming born-again virgins, there's Dean talking about why sex is awesome...to a purity group.
"The Spirit of Las Vegas": Sam gets rid of the cursed Japanese coin (and the God of Poverty that's been dogging Dean) by force-feeding it to Katty the casino robber. I blame the language barrier in the original Japanese production for them not making a "This too shall pass" joke.
"Moonlight," the adaptation of the episode "Heart," includes Dean uplifting the serious business of waiting for to see if Madison transforms by breaking into a dance and the tune of "When The Saints Go Marching In." It must be seen to be believed.
Many, many of the DVD commentaries, but especially "The End". Particularly when Eric Kripke, Robert Singer, and Ben Edlund make fun of Samifer and his shiny white suit, their own habit of having monsters monologue to the Winchesters, and how they should end every episode with the boys scrubbing down the sites of monster attacks so they don't leave forensic evidence behind as they angst. "You were mean to me back there." "I know, I'm sorry!" "Pass me the bucket." "I won't, damn you!" "Why, something wrong?" (Complete with growly impersonations of the Winchesters.)
The bloopers for this show are some of the best for any tv series. This show stars a bunch of unabashed dorks, and the gag reel bears witness to this.