Your first conversation with your mom in the first generation games. "All boys leave home someday. It says so on TV." The notion of Delia Ketchem saying something like that brings a smile to my face.
In Pokémon HeartGold and SoulSilver, sometimes Juggler Irwin will call you and say this:
You know, every time I recall your escapades, [player name], I am just so deeply moved by them. *Click ...............*
He originally stalked you, to help alleviate Now, Where Was I Going Again?. Which is either made creepier or funnier by what he said when you beat him (changed for HG/SS):
Oops, dropped my balls!
"I like shorts! They're comfy and easy to wear!" This single line spoken by a trainer in Pokemon Red And Blue has spawned a whole lot more "shorts" trainers.
"Hey Kid, wanna see my Pokémon?" Infinitely more funny if you imagine the speaker as a creepy child-molester-type.
HeartGold/SoulSilver has one in the underground path between Cerulean and Vermilion. There's a guy who starts the conversation by assuring us he's not a bad man, then starts going on about how places like this attract bad people and how angry it makes him. If you bought a RageCandyBar in Mahogany Town, he'll notice it and ask for it, and if you give it to him (which, seeing as how it's just been taking up space in your Key Items pocket, is a good idea), he'll appear to get angry at how good it is. He'll then thank you by giving you TM64, which contains, in his words,
tick-
tock
tick-
tock
tick-
tock
tick-
tock
tick...
..................
..................
Ka-Boom!!
Sign in the Team Galactic headquarters: Make sure the bed is unoccupied before getting into it. (One wonders what kind of Noodle Incident made that sign necessary...)
"Light years is a measure of distance! Not time!"
Even EV training can result in funny things. For example, you're battling Zubat to raise your mon's Speed stat, and you level up. You get "Max. HP + 3, Attack + 3, Defense + 1, Sp. Atk + 2, Sp. Def + 2, Speed + 14". This can be funny the first few times you see something like it.
Unfortunately, no longer the case as of Generation V; stats are recalculated after every battle, regardless of whether or not the Pokémon leveled up, meaning that such dramatic stat jumps no longer occur.
One from the Dark Cave in HeartGold/SoulSilver, when talking to my walking Pokémon: "Jacob seems a little cold..." For the record, Jacob is a ghost. So, yeah, I'd think he'd be cold. Thanks, Captain Obvious!
Several of the phone calls you can get in HG/SS, but especially the ones from Gym Leaders. This includes Chuck deciding to take his wife to Tojoh Falls, Falkner and Janine's war, Clair thinking her outfit is the latest fashion, and Whitney rambling on about nothing.
Chuck's other phone calls are good as well. In particular, one of them has him talking about how his waterfall-generator has been malfunctioning, only to be cut off by it breaking and gushing water everywhere.
From Pokémon XD, we have the nonsense that is the Hexagon Brothers. The first time you meet them, they try to count off, but the one counting forgets to count himself, resulting in them waiting for the "sixth" one to show up. Next time, they stand in a circle and count, resulting in counting several of them more than once, and suspicions of spies. When you meet them the last time, they've finally learned to count (Backwards), but are now trying to impersonate the same person.
From the Sinnoh games: "Team Galactic will have that honey! We must have it to attract Pokémon in great numbers!"
And after you beat those two grunts: "This guy's tough! Like, really really tough! Tougher than I can put into words, and I know a lot of words!"
Any time an enemy Pokémon uses Selfdestruct or Explosion when you have a Ghost-type out. There was one trainer in Pokémon Stadium 2 that liked to use such moves until it became a 1-on-1 battle. For eample, a rental Haunter vs. the opponent's Forretress. With all of the enemy's attack moves being either Bug type (which does 1/4 damage to Haunter) or Normal type (which does none) and the rental Haunter's only direct attack move being the Grass-type Giga Drain (which does only 1/4 damage to Forretress and has horrible PP), the battle more or less can come down to repeatedly using Spite on the Forretress to run it out of PP until it has no choice but to use Explosion.
In the third gen games, there's a Collector right outside the Rustboro entrance of Meteor Falls, who has a rare Pokémon. In Ruby, it's a Seviper. In Sapphire, it's a Zangoose, and in Emerald, he has both. After you beat him, he says, "You...You want my Pokémon, don't you?"
The more recent generations have added a bit of humor in the actual story. The Diamond/Pearl/Platinum rival is always good for some laughs due to his impatience leading to him constantly crashing into the player character, and Platinum adds Funny Foreigner Looker and batty old Starscream Charon to the cast of characters.
Your rival's constant crashings gets kicked up a notch when you are introduced to his father, Tower Tycoon Palmer, because he also greets you by crashing into you. (Apparently, it runs in the family. Literally.) And then, after commenting on how it's been a while since he saw you and how "he must not be far behind", he runs off...at which point, sure enough, your rival comes running in a couple of seconds later and crashes into you.
Hit 2 times!
And there's the first word that comes from your rival when he meets his father.
"DADDY?!"
There's also his outrage at not getting a Pokédex from Professor Rowan, only to be told that he would've gotten one if he hadn't run off so fast.
And while you're in Pastoria in Platinum, he goes behind the Croagunk poster and laughs about his new style.
"Are you enjoying your unescorted, unauthorized, and unsettling tour of our HQ?" - Said by a Galactic Grunt at the HQ in Veilstone.
Black and White has a double battle in Big Stadium with a pair of trainers whose introductory line asks if you want them to tell you about the offside rule. Upon talking to them again after their defeat, they each stammer and eventually say that the other one will explain it. Anyone who has ever played or watched association football will appreciate this exchange.
In Black and White, a female Swimmer in Undella Bay asks you something along the lines of: "Did you come to see Cynthia in a bathing suit too?" Then, when you win the battle she mentions how often Cynthia swims in the bay.
Driftveil City also has an interesting trainer. "I'm a heartbreaker. My name...Charles."
The Mistralton City gym involves getting into cannons and blasting yourself around the gym. The second-to-last cannon shoots you all the way across the gym—and into the facing wall. SPLAT! Even better, you slowly slide down the wall onto the platform beneath.
Abusing the Trendy Phrase feature in Dewford Town. You can make them say things like "YOUR MOM", "ADULT ANIME", "TIGHT REAR", etc.
When you rematch Lt. Surge in HeartGold/SoulSilver, one of his Pokémon is a Pachirisu. LT. SURGE WITH A PACHIRISU.
The satisfaction you get from giving your rival (if you have the option to name him) a stupid name. "That's right! I remember now! His name is DOUCHE!"
In Emerald, Scott drops by the Oceanic Museum after you drive away Team Aqua. Thinking that you have potential as a trainer, Scott practically begs to be registered in your PokéNav. The game then has this interesting dialogue box pop up.
Registered this Scott person in the PokéNav.
In DPPt, there's a particularly deranged Hiker in the battle tower who has a thing for Miltanks. Specifically, his ending quip:
The episode where James is trying to avoid being dragged back to his mansion home by Jessie and Meowth. He stalls with a tragic story about running away in his childhood, in the winter, with only his faithful Growlithe by his side. Somehow, it ends with him freezing to death. Dog of Flanders, anyone? Cue the heartwrenching music and waterfall tears.
A hilarious yet shocking case of Getting Crap Past the Radar in Lorelei's showcase episode..."I know what she's doing! It's...it's...perverse psychology!"
The Advance Generation episode Berry, Berry Interesting: there's never a serious moment here. Best part is the moral: never allow May to make food for the Pokémon.
May's first try at Pokéblocks had Combusken lying face-down on the ground. Well, Beautifly liked them...
It didn't just drop Combusken, it KO'ed Ash's entire team. Not even Tobias and his team of ubers flattened them that quickly.
Oi! Those were extenuating circumstances!
Jessie seemed to like them, too...
From the same episode, Wobbuffet playing...ninja*
well, close enough, anyway
.
Also from the same episode: Munchlax being caught with a Pokeball...inside its mouth.
During the Kanto Pokémon League...
Misty: "You can stuff your greedy little face after we find a Pokémon Center!"
Even though it's been used for Shipping proof, this exchange from Poké Ball Peril is hilarious. To set it up, Ash and Misty, who are traveling without Brock, have been captured by Team Rocket, and the Terrible Trio takes notice:
James: Jessie, I think we've accidentally captured a pair of very romantic creatures in our little cage!
Jessie: (making lovey-dovey eyes) You mean? Daaaaawwww!
Meowth: Dey're loveboids!
Ash: (Ash and Misty look at each other for a second before turning away, blushing) You're crazy!
Jessie: (Jessie and James are doubled over while Meowth is rolling on the floor) But you're blushing!
James: Kissy, kissy!
During one of Team Rocket's thefts at a clinic (in the AG episode Delcatty Got Your Tongue?), they dress up as Swiss hikers (ridiculous accent included), with Meowth practically mummified in bandages:
The way Corphish defeats Katie's Golduck in the Hoenn League is this and possibly its Crowning Moment of Awesome — managing to listen to Ash while confused, it swims up behind Golduck and...cheerfully shakes its hand. Then uses Vice Grip to shake it harder, then spin it over its head, and finally throw it to the other side of the battlefield to set up for the deciding Bubblebeam. That's right — Corphish defeated an opponent by beingitself.
Despite it not being the punchline, Misty's fake name from episode 42 of the Swedish dub:
Pikachu also refused to fight Misty during Ash's Cerulean gym battle. The humor is not so much the refusal as how Ash was about to throw him into the arena overhand, like a Pokéball.
In DP 157, Gotta Get A Gible!, Gible is caught by one of Team Rocket's Humongous Mecha. They jump over a canyon to get away from Ash, and he runs to the point where he ALMOST makes it over the canyon when he jumps. Ash used ExtremeSpeed! ExtremeSpeed missed!
As a bonus, he has Pikachu jump on his head before he makes the attempt. Tip for all Pokémon Trainers: Pikachu is nota bunny hood!
DP 164, Pochama (Piplup) Goes Astray!, has a rather brilliant moment that serves as part of the episode's plot. Piplup always ends up on the receiving end of Gible's failed Draco Meteor attacks, and eventually has a go at it. When Gible then decides to try to nom on Piplup's head...well, let's just say that the penguin Pokémon finallysnaps (Skip to 3:20 for the scene in question). This is followed up by Piplup envisioning Ash and Dawn scolding Gible, and how Piplup sees Dawn.
Not to mention that, when Piplup snaps out of its delusion, we see that it's actually been nuzzling up against Pikachu, who is just sitting there with a -_- look on its face. It then pats Piplup on the head in a "there, there" sort of way, then runs off to be with Ash, Dawn, and Brock.
Ash's Gible is pretty much a walking Funny generator. In one episode, Team Rocket are about to get into their newest Giant Mecha, only to find out that Gible has already eaten it.
In the episode Where No Togepi Has Gone Before!, the main villain is a Togepi that's causing trouble. It's used Attract to take over Pikachu, Piplup, Croagunk, and Meowth. Brock's solution? Call out Happiny to smack all four of them back to normal.
When Togepi uses Attract, it also hits Jessie's Yanmega. The attack doesn't work, and once Brock explains that Attract only works on targets of the opposite sex, Jessie freaks out about the fact that her Pokémon is a female. Yanmega blushes in confirmation.
Paul's jerkassery can be so deliberate and mean that sometimes it's just plain hilarious. In one episode, he's trying to capture a wild Drapion when Ash's Gligar comes flying toward him, unable to stop itself; whereas Ash would try to catch it, Paul simply moves out of the way, and Gligar flies into the rock that Paul had been standing in front of. Look for it at 4:05.
In the ending to For The Love Of Meowth!, for the sake of his Glameow love interest, Meowth takes down Seviper, Infernape, Togekiss, and Yanmega using Fury Swipes. Then Glameow evolves into Purugly, and when Meowth figures it out, various things break down, such as a building, a big heart, and even a statue of himself! Hilarious.
From the first episode:
Dexter: Rattata: the forest Pokémon.
Ash: But this isn't a forest. It's an open field!
Dexter: Sometimes, it comes to open fields to steal food from stupid travelers.
Even better, Dexter emphasizes the word "stupid," so it is openly insulting Ash.
The episode True Blue Swablu! has a scene in which the group try to help a injured Swablu regain its confidence to fly back by saying that May's Beautifly uses a 'magic powder' that grants those coated in it the power of flight. After Swablu 'tries' it and starts flying again, Ash and Pikachu attempt the same thing:
Ash: Wow, that magic powder is great! OK Pikachu, we're up next!
Pikachu: Pi-Pika!
*May, Brock and Max look at them in disbelief*
Max: The magic powder's fake, Ash...
Ash: No way, it looked like it was totally real...
Max: Totally real, all purpose FLOUR!
Pikachu *blushing slightly*: Pi!? Piiikachu...
And from the same episode, when Team Rocket steal the Swablu, May tells it to use Sing on them. Before they all fall asleep, James tells Cacnea to use Pin Missile. It falls asleep and into the balloon basket - then unleashes the attack, resulting on Jessie and James getting their asses spiked, and Meowth and Wobbuffet having their heads needled. Needless to say, this wakes them all up, and when James tries to get Cacnea to stop, he finds that it's using the attack WHILST asleep and thus can't make it stop. Not until it damages the balloon, anyway.
The start of the episode has Ash and the group once again lost for the umpteenth time:
May: "We're getting pretty good at being lost!"
Max: "So why don't we just turn around and retrace our steps?"
Brock: "Then we'll be lost going backwards!"
And one more from this episode is Torchic's method of waking up the group after Swablu puts Ash and friends to sleep. We see it from a first person perspective pecking them, all the while with a happy look across its face.
A scene near the beginning of the episode What You Seed is What You Get! has Team Rocket trying to steal some watermelons from a field. Jessie notices what looks like a giant watermelon rolling towards them - only for them to find out that it's a disguised Electrode which proceeds to send them flying.
Meowth: "TALK ABOUT YOUR FORBIDDEN FRUITTTTTTT!"
The girl who works at that watermelon farm assumes Ash and his friends are watermelon thieves. She (and in full seriousness) lashes out at him by chomping down on a big piece of watermelon and then spitting a stream of seeds right in his face. Ash is more irritated than anything.
The end of the episode, Ash and Pikachu trying to cheer Treecko up. When it ignores them, they decide to spit watermelon seeds at it. The end result of this is a ticked-off Treecko perfecting Bullet Seed - with Ash as its target!
Then there's the climax of the episode Bye Bye, Butterfree. After Pikachu jumps off of Butterfree and lands on the cockpit window of Team Rocket's helicopter, it gives a loud "Ka!" and a smile as it begins to use Thundershock. As it gets closer and closer to unleashing the attack, Team Rocket repeatedly says "HE'S GONNA SHOCK US!", with the sentence getting higher in pitch and more hysterical each time.
In Sparks Fly For Magnemite;
Ash: Magnemite is following Pikachu all over the place, almost like it's a streaker!
Brock: *blushing profusely* A-Ash, you mean a stalker!
Ash trying to catch a Pidgey in the first episode of the animé.
The various times Jigglypuff put the crew to sleep. Good times...good times...
Probably not intended, but in the Japanese version of the episode where Ash gave away Gliscor , Ash was smiling as he was giving it away in a very "It's finally gone, gone, gone...I'm finally alone again..." way.
Anything Byron says in Dealing With Defensive Types. Played as an ENORMOUS Ham by Dan Green, and constantly yelling about how much he loves things, such as his Steelix, Defense, and Fossils. Complete with random explosions every time he proclaims his love.
Bonus points for his opinion of Team Rocket, which emphasizes their talent at digging exquisite holes and ignores their attempt to run off with his fossils.
After going to investigate a noise in the room where Byron keeps his fossils:
Roark: Somebody dug this hole!
Byron: I don't believe it! *long pause* I love this hole! *everyone else collapses*
Ash: You do?
Byron: Give it a good look! Look how perfectly shaped it is! How it slopes gently downwards! Whoever dug this hole has the skill and the craftsmanship of a fearsome hole-digger! *everyone else collapses* I must find the artisan who did this! Think of what it would do for my excavations!
Roark: Dad, you better have a look over there!
Byron: It can't be! *points to other hole* Closer examination reveals this hole was dug bya machine. *everyone else collapses*
Roark: Can't you see that all your fossils have been STOLEN!
Byron: Stolen? Nooo! My precious fossil collection is gone!
One Advanced Generation episode features (yet another) Team Rocket split, with the added twist that they come across one of Cassidy and Paunch's plans. Before the episode is over, they've temporarily managed to switch pairings. Complete with mottos.Click.
Jessie and James doing their introduction speech while talking to Giovanni on the phone in Island of the Giant Pokémon.
Best Wishes has already had a large number. The first: Ash testing out Pikachu's newly-recharged electric attacks by having Pikachu use Thundershock and Volt Tackle on him. The Volt Tackle ends with him woozily saying something, then falling over twitching. Then the entire meeting with Iris, and him climbing up a tree and then jumping into the air to try and rescue Pikachu and Axew, before missing while trying to grab the glass cage and falling back down to the ground.
Dawn's Early Night: Ash's reaction to finding out that the Hearthome Gym Leader isn't available for a Gym Battle is crashing right into the door. And all of his Pokémon do it too. While Nando (who had informed Ash of the Gym Leader's departure about three seconds earlier) just stares at them in the background.
Another contender for Mood Whiplash. How do we find out Ash's Grovyle is in love? A flower randomly popped up in his twig! Not to mention how he acted around her!
During the preparations for the Kanto Pokémon League, Team Rocket tries to capture a Mr. Mime, and they realized they actually captured Ash, who was wearing a Mr. Mime suit, and he steals their balloon.
In the ninth episode of Best Wishes, the beginning shows Axew's first onscreen battle. Cilan's Pansage...beats it in a Curb-Stomp Battle while still going VERY easy on the little dragon.
And right after that, when Axew attempts to get serious. Axew charges his Dragon Rage up in such a dramatic way...and then sneezes. Needless to say, the whole place within a ten foot radius is a bit decimated, leaving everyone burnt and twitching.
At the end of the episode, Iris has had enough of Ash challenging her and Axew, and tells him that he should be the one to battle Pikachu himself. Ash proceeds to do just that.
Team Rocket's attempts to open a Clamperl Shell in Clamperl of Wisdom.
This is followed by a classic image of chibi-Giovanni stubbing his toe on the shell.
All of the Giovanni fantasies that Meowth comes up with to convince Jessie and James why capturing each episode's featured Pokémon is a good idea. Just...everything about them. The often ludicrous content of them (especially the ones with chibi!Giovanni), the fact that they exist at all, the fact that Jessie and James almost always find them convincing somehow...
With one hilarious exception. For whatever reason, they somehow think that Giovanni would have no use for Lucien's Bronzong.
When Meowth is infatuated with a Glameow, he tries to convince Jessie and James to get it from the trainer using a hastily-created Giovanni fantasy. Even they immediately point out the holes in it.
From The Bicker the Better, James sings a song, composed of one word, over and over and over: "Ugly Ugly Ugly~!"
Not to mention the insanity that was Ash/James vs. May/Jessie later in the episode. Meanwhile, Brock's the Combat Commentator, Wobbuffet imitates his every move.
Too bad we didn't get any Ash/James or May/Jessie mottos...
From Hocus Pokémon: Ash gets turned into a Pikachu. Enough said.
From An Old Family Blend: "Yeah?! Well, that means it's your fault! I want a fine in ten seconds! Nine, eight, seven, six, five, four-"
Faced with Team Rocket's Humongous Mecha, Ash decided to call on his Snorlax to literally take it down (since Ash used a similar tactic a hundred episodes back, during the beginning of the Battle Frontier saga). Then they found out that Snorlax had gone to sleep. That's not the hilarious part; what's really hilarious was that Snorlax really did take the mecha down (albeit temporarily), by rolling over it.
Poor Bulbasaur. The only one of the originals to appear, made worse since it involves him getting raped by Heracross, again!
From Where No Togepi Has Gone Before after Rayquaza blasts Team Rocket's spaceship (with everyone aboard) and the emergency parachute is incinerated:
Claydol, Big and Tall: the gang and Team Rocket dress up in different costumes to distract the giant Claydol, and the Claydol fell in love with...Wobbuffet in a MAID COSTUME!!
Immediately after this, an old man who was helping everyone reads them a story about another giant Claydol being stopped by a Wobbuffet. Cue this exchange...
Jessie: I'm started to have my doubts about this...
May: (deadpan) The text, or the guy reading it?
There is a place in the anime called...*snicker*...Hop Hop Hop Town!
It's a literal translation of its Japanese name, Yoyoyo Town.
Pikachu and ketchup. There's a reason why it became the rodent's Never Live It Down after Showdown at Dark City.
Jessie catching Seviper without using a single Pokémon...and succeeding!
I think that costume came right out of his closet.
Jessie's "WTF" expression during that line was priceless.
Wheel Of Frontier: it's Narm Charm, since it managed to be both Funny and Awesome, but Snorlax snags a win for Ash...by literally flattening Greta's Medicham!
Episode 17 in the Best Wishes anime: Ash's Scraggy finally hatches from its egg. After a nasty encouter with wild Galvantula which leaves it paralyzed, Ash is forced to feed it some medicine. Watch for yourself (skip to 1:54 in the video).
Gliscor's antics in the episode Doc Brock; from volunteering to be the one to fetch Brock (Staravia got selected instead), and Brock attempting to carry it on the back (too heavy, so Brock had to leave it behind, promising to go back to Gliscor later). But then, the gang forgot all about Gliscor until the very end of the episode!
Anytime someone messes up Butch's name and him correcting it (many mess ups include Hutch, Buzz, Batch, Klutz, Potch, Mitch, Chuck, Huoch, Fuch, Botch, Butcher, Biff, Buffy, Bill, and Bob).
Or, specifically, when he himself got his name wrong when someone said it right.
Or, someone getting his name right and Butch flipping out anyway...only to catch himself mid-sentence and mutter, "Oh, that's what you said..."
Even Bulbapedia went along with the joke: a lot of the wrong names are redirects to his article.
At the end of the really old Kanto episode Tentacool and Tentacruel, Misty makes the V-sign toward the camera while holding her new Pokémon, Horsea, and Ash complains, "Wait a minute, that's supposed to be my pose!"
A wild Minccino using Tickle on Bianca's Pignite in BW013. That is all.
And then using Attract on Ash's Snivy.
We also see that same Pignite acting a lot like histrainer. It's too much for words.
Cilan crying over Bianca dirtying his cutlery; it's not something you'd expect from him...
The Minccino stuffing Ash's badge case in its mouth.
Gone Corphishin': Ash, Pikachu and Brock are proudly boasting that they have "experience" in falling into Team Rocket's pitfalls. May and Max quickly point out that that's not something to brag about. Cue all three going into a Corner of Woe!
The shame.
Later, Team Rocket fall into the gang's trap, and when discovered they recite their motto. May and Max (again) point out that they're literally not in the right place to recite their motto. What's Team Rocket to do? Go to the same Corner of Woe, that's what!
Electrode may be the single fastest Pokémon in the original 151, but the episode does a good job showing us what using one in a race would be like: even more Epic Fail.
Once in a Mawile: Ash's Corphish goes Dogged Nice Guy and starts wooing the episode's featured Mawile; it has to be seen to be believed. Then he faces utter rejection, and Brock, fittingly, sympathizes with him, and gives him a Rousing Speech of some sort. Then they both start crying, and Torkoal just randomly joined in for no reason!
Later in the episode, Team Rocket captures Brock's Lombre instead of Mawile, and Meowth has a hard time imagining what kind of use their Boss would have with him. Fellow idiot Wobbuffet comes out, and he and Lombre "bond" through a comedy routine.
Love at First Flight: Brock's "girl-radar" fails and he starts going after...Ash in his second crossdressing stint.
To Master the Onix-pected: the most awesome way to Break The Fourth Wall: Meowth fast-forwards the Team Rocket motto!
Jessie: That was exhausting.
James: I think I bit my tongue.
Any time Ash acts like a five-year-old.
Ash: *whining* I am not a baby! Am I, Pikachu?
The beginning of Exploud and Clear has May ask Ash which Pokémon he's going to use for his upcoming gym battle. Ash says that, whichever he chooses, his Pokémon are awesome. We then get to see just how "awesome" they are for the moment...
In the fourth episode of Best Wishes, Meowth is disguised as an Umbreon to provide a distraction. When he is finally cornered, his pursuers burst into tears of joy from "discovering the first Umbreon in Unova." This makes Meowth feel guilty, so he confesses that he is really just a talking Meowth. Only after he escapes do the pursuers realize that a talking Meowth is also rare, leading them to burst into tears once more.
On several occasions during the Diamond & Pearl seasons, Cynthia is shown to be rather...indecisive when it comes to snacks. The first time this happens, it prompts Meowth to comment: "Imagine her at the grocery store!"
Steamboat Willies: the Pokémon start a band. Epic Fail ensues.
Top-Down Training has Croagunk doing his usual "job" when Brock goes to flirt with Cynthia, but then Cynthia merely stops him with a quick glance. Croagunk blushed.
All Dressed Up With Somewhere To Go! has James try to use Mime Jr.'s Teeter Dance to stop our heroes from chasing them in their hot air balloon. It ends up confusing Dustox and Meowth instead - and Meowth is the one steering the balloon! It's also tied with the following:
Meowth: First the movie short, then TV and now this!
BW029: Cilan screaming like a little girl. That. Is. All.
The Kanto episode Showdown in Pewter City has Team Rocket setting up a pitfall trap at the start of the episode - then forgetting where they placed it, which leads to them falling into it, getting buried seconds later. They reemerge at the end of the episode, only to be trampled on by Ash, Misty, Brock and Pikachu.
James: I told you I'd get us all out of this!
Jessie: This was all...*the three are all stepped on by our heroes* ...your fault!
And a few seconds later...
Jessie: Buried alive and trampled...
Jessie & James: We've hit rock bottom! *The three of them all fall back into the pit*
Bucking the Treasure Trend! has a scene in which the group get seperated from Piplup and Buck after getting attacked by Graveller. After fighting off a Golem with Gible, the group say they have to find Piplup. The method they use? Gible using Draco Meteor, to Dawn's dismay. It works of course, with Piplup taking a hit for its troubles. And to top it all off, Piplup rather begrudgingly thanks Gible for its help.
Misty's god awful makeover by Team Rocket in Pokémon Fashion Flash, and the kicker? Misty loved it.
Ash & Brock: What happened to her face?! (desperately holding in their laughter.)
The episode when the gang returns to Pallet Town after their adventures in the Orange Islands. Instead of A Tents Situation, it should be renamed to Muk raeps EVERYBODY.
Whenever Professor Ivy is mentioned to Brock. He goes sulking.
Ash even does that when Misty mentions Gary's name!
When Team Rocket bound and captured them, Meowth's curiosity got the better of him, and continues to pester Brock on why he left Professor Ivy; Brock managed to get out of his bonds and reappear on Team Rocket's high wire!
Ash presents his mother with his Orange League trophy. What does she do with it? Use it as a dumbbell.
Cabernet's Imagine Spot of Evil Cilan, complete with the evil laugh. Pansage's menacing expression in the background also helps.
At one point, she attempts to evaluate Ash's Snivy by licking her.
Iris and Georgia's interactions as rivals. It's basically a Cat Fight without any actual fighting, and it's hilarious.
A lot of things Barry says and does.
The mere picture◊ that instantly launched ValleyShipping where Charla cuddles up to Ash's Charizard while the latter is standing tall and proud. Makes a person burst into laughing fits just looking at it!
In BW041, Ash is trying to get Trip's attention and is waving him over to the group. Trip obviously sees Ash via his camera lens but then decides to ignore him after he looks directly at Ash. The expression on Ash's face is priceless.
Iris getting a bad vibe from her first opponent, someone wearing a Watchog costume.
Why was Staravia out of action for most of Jumping Rocket Ship? He instantly fell in love with a decoy!Staravia, that's how! Doesn't help that every time the scene briefly cuts to him, he's going Brock for "her"!
Ash's Snivy was alternately made of this and Badass in Emolga and the New Volt Switch. Usually by using her Vine Whip to discipline the kinda-Jerkass Iris' Emolga. The part where Emolga tries to sneak away from the battle with Simisear (that she caused) and gets grabbed, as if Snivy's saying, "I'll deal with you after I take care of this." is hilarious.
This episode also has Chivalrous!Oshawott who, being the Butt Monkey of Ash's Unova team, fails at looking cool.
From the episode before (Emolga the Irresistable), Iris' (soon to be) Emolga spreads Attract onto a flock of Swoobat (it fails on the girls, of course). It also affects Excadrill!
A few minutes later she's thrown into the water and emerges as some kind of horrifying lake zombie. The Thing from Psycho Lagoon!
Meowth: Look away. Maybe she won't notice us.
In BW044 after chasing down Zorua for three episode straight, Bianca finally catches her. Zorua, GIVES UP running away from Bianca and Bianca later on that night puts clothes on her which is a reference of the Pokémon Musical. Zorua is not amused.
Later on in the episode, Bianca taunts Luke into making him move closer to watch Ash and Iris battle. It works.
Cilan and Burgundy's "Tasting Time" duet. Enough said.
The end of BW046. The Purrloin that Meowth and Oshawott fell in love with turned out to be a male. Their expression is priceless.
In BW052, Ash needs to be reminded that Palpitoad was only his first knocked out Pokémon and that he's allowed two more...and he leaves the Gym because he didn't bring any others! Cue Elesa's WTF look.
In the same episode, after Snivy and Emolga are unaffected by Attract, Ash proves just how off his game he really is:
Ash: It didn't work!
Elesa You're right; by any chance, would your Snivy happen to be a girl?
Ash (looking completely embarrassed): Argh, of course! I totally forgot!!
(Cut to Iris, Cilan, Pikachu and Axew with disbelieving expressions. Cue Face Fault.)
Iris (eyebrow twitching): How many times will it take for Ash to learn that Attract doesn't work between girls!?
Cilan: Good question, although this is Ash after all!
Pikachu and Axew (sitting with their backs against each other, sweatdropping): "Pika..."/"Axew..."
Elesa: Emolga may be an Electric-type, but it's also a Flying-type.
Ash: Huh...and Flying-type moves are strong against Grass-types...(realisation dawns on him, followed by Oh Crap expression) OH MAN, SNIVY'S A GRASS-TYPE POKéMON!!
Ash manages to be so close the Champion of Unova...until everyone realizes that Alder was actually sleeping.
Ash is at the Safari Zone, which is a familiar place to all who played the game. He got 30 Safari Balls. What he get at the end? 30 Tauros.
Ash LOVES food. We all know that. Recently, it seems to have become something of a Berserk Button for him and Pikachu to see it wasted, judging by their Nightmare Faceshere. Completely out of left field, man.
May has one too, during her return episode in Sinnoh. This leaves Dawn to comment whatever happened to the "Princess of Hoenn".
Ash, his friends and Team Rocket are attempting to wake a sleeping Snorlax when one of them comes up with the idea of invoking True Love's Kiss. After a failed and undesired attempt by Psyduck, Team Rocket prepares for their attempt. While it turns out to be Meowth in princely regalia, and his attempt gets an explicit negative reaction from the Snorlax, it's better than the alternative.
The Wacky Watcher, which is a filler episode about Magikarp...that just so happens to throw in a Groucho Marx expy as the titular professor. Cue 22 minutes of goofy wordplay and slapstick.
The mere sight of Tepig and Oshawott in afro wigs is enough to make people laugh BEFORE the episode aired.
Snivy absolutely refusing one also warrants a mention.
In Battle of the Badge when Team Rocket show Togepi to Giovanni. His face is priceless.
At the beginning of Battle Aboard The St. Anne there is an extended scene where Team Rocket are hyping up the gang to go on the ship. After their speech, Ash turns to Misty and says "Do you know anyone who says 'radical' anymore?"
Cilan and Stephan cosplaying as Elesa and Nurse Joy, respectively. Cilan can pull it off. Mostly.
Minor one, but seeing Team Rocket root for Ash during the Sinnoh League Victors season was worth a few chuckles.
Scrafty's method of kidnapping Axew in Meowth's Scrafty Tactics - it shoves Axew into its pants.
In DP, when Kenny first meets Dawn's friends, he shares embarrassing stories about Dawn from when they were 5 - like how she tried to "fix" a haircut she hated and ended up looking like a Chimchar, or when she sneezed during a school production. Ash, Brock, Pikachu and Piplup looked to be nearly bursting from the suppressed laughter each time - and laugh precisely when she shouts at them indignantly!
Then Kenny mentions Dawn coming to school in pajamas and mismatched shoes. You could hear people laugh at that from space.
When the story of Dawn's nickname "Dee Dee" finally comes out, it's not meant to be viewed as funny but Dawn's sheer trauma over the incident kind of makes it so. Even Ursula was laughing her butt off over it!
This exchange in BW 76(they're walking through a durants' nest):
Iris: "Make sure not to bump your heads."
Cilan: "Got it. *promptly knocks his head against a low stalactite.*"
And later continued—
Iris: "Watch your feet."
Cilan: "Yeah. *immediately slips and falls on the ground, complete with sound effect.*"
In Pokemon Heroes either Bianca or Latias kisses Ash out of nowhere. Seeing Misty and Brock Face Fault is funny enough as it is, but then you notice that Misty has dropped Togepi. That means she has gone beyond Face Fault into total Heroic BSOD territory. And it takes her a good minute to reboot.
