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.
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 himfreezing to death. Dog of Flanders, anyone? Cue the heartwrenching music and waterfall tears.
Then, when Jessibelle reveals her kinky torture room, Misty can be seen blushing profusely. Blushing over what?!
A moment later, Jessiebelle is chasing James around the room with a bullwhip. His parents are calmly sitting at a garden table in the middle of the room, drinking tea. And the twerps are also watching this spectacle, providing this gem of a line.
Ash: Shouldn't we try to help him?
Brock: Nah, I don't like to get involved in these little family squabbles.
In the episode's beginning, as Team Rocket read the sign with James' picture on it:
In Electric Shock Showdown, apart from Lt. Surge's pricelessFlat "What." upon Pikachu avoiding Raichu's attack by grinding its tail against the ground, there's also Team Rocket and their snarky commentary.
Brock: (on Pikachu) It used its tail as a ground, and dodged the electric shock!
Despite it not being the punchline, Misty's fake name from episode 42 of the Swedish dub:
Brock: Caesar Salad.
Misty: Ann Ananas. (Anne Pineapple, also a possible reference to Anna Book, the voice actress.)
Ash: Tom Atsĺs. (Tom Atosauce.)
It's even funnier in the English dub, where Misty's name is "Ann Chovie".
"Thank you for your wisdom and advice, Tom Ato!"
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.
Jessie and James doing their introduction speech while talking to Giovanni on the phone in Island of the Giant Pokémon.
"Pikachu is unwilling to battle!"
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.
From Hocus Pokémon: Ash gets turned into a Pikachu. Enough said.
I think that costume came right out of his closet.
Jessie's "WTF" expression during that line was priceless.
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!"
There is a place in the anime called...*snicker*...Hop Hop Hop Town!
It's a literal translation of its Japanese name, Yoyoyo Town.
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*
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.)
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.
From the same episode? When Team Rocket reveals themselves during the race, everyone is glaring at them with determined stances. Everyone except Squirtle and Pikachu, who're ignoring them to chow down on the food the racing Pokemon are supposed to eat.
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?
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, 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.
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?"
The Ditto from "Ditto's Mysterious Mansion". When Jessie demands that it turn into a Dratini, it turns into the book the Dratini is pictured in instead.
In "Who Gets To Keep Togepi?", Team Rocket temporarily gets ahold of the unhatched Togepi's egg. Meowth cares for it like it was his own child, but James constantly makes crass comments and jokes about eating it, which leads up to this:
Meowth:(polishing the egg with a cloth) Rise and shine, my little eggy-poo. Meowth's gonna make you nice and shiny 'cause we got a lot of inca-batin' to do.
James:(hands Meowth a plate with scrambled eggs on it) Here.
Meowth: What's this?
James: Your scrambled eggs.
Meowth:(turns furious, then hits James with a frying pan) I told you ta lay off the E-G-G-S! How could ya be so insensitive, ya numbskull?!
The first episode has this gem.
Ash: Is it because you don't like me?
Pikachu: (nods his head) Pika Pika.
Ash: Well I like you a lot. And since you're the first Pokémon I'm training, don't you think you could be a little nicer and open your mouth and tell me what's wrong?
In "Make Room For Gloom", after a confident Florinda thanks Brock for helping her believe in herself and feels ready to run her family's nursery, as long as a special someone is around to share it all with her, a lovesick Brock turns his back to her and goes into a blissful spiel with quite amusing results.
Brock: This is so sudden! I've always dreamed of having somebody like you, someone as kind and talented and beautiful as you are, and now you've made all my dreams come true! Yes, Florinda, darling, yes! I'll share my life with you! (turns around to find himself looking into Ash's eyes instead of Florinda's)
Ash: Hey, Brock, are you talking to somebody?
Misty: I think maybe you had a little too much of that antidote.
(Brock turns to see that Florinda has already proposed to her true love, Potter.)
Brock:(visibly distraught) Rejected by the one girl I've loved! I'll never find another one like her again!
Ash:(trying to console him) Cheer up, Brock, you'll find plenty of other girls to reject you!
Anything involving the Gastly from "The Ghost at Maiden's Peak", from the Venustoise illusion, to the quip about making some quick bucks by helping the spirit maiden. Plus, this exchange:
Gastly: What is that?
Misty: It's a cross! I also got garlic, a hammer and a stake!
Gastly: Ugh! What do I look like, a vampire or something?
"Mystery at the Lighthouse": When Krabby's Poké Ball vanishes, Misty and Brock explain to Ash that it was sent to the place he got his Pokédex from. When Ash realizes via flashback where it is...
Professor Oak: HERE'S YOUR PIKACHUUUUUUUUUUUUUU!
Haunter vs. Kadabra: As Sabrina's father is explaining his daughter's backstory to Ash, he shows him a picture of their family.
Ash: Sabrina had this picture of her family in her room. If you have the same picture, then that must mean you're...
Sabrina's father:(thinking) Does he know? He must have figured it out by now. After everything I've said, he must have figured out the truth about Sabrina and me. He must realize that I'm Sabrina's father.
Ash: Then that must mean you're a photographer!
Sabrina's father:(flies off the bench)
Later, after Ash has defeated Sabrina...
Ash: But if you've known Sabrina since she was a little girl, then that means...
Sabrina's father: So you figured it out, eh?
Ash: Then you must have taken her baby pictures too!
In "Ash Catches A Pokemon", when Ash, Misty, Pikachu, and Caterpie are settling down for the night, Misty's being her typical big-mouthed, bitchy self telling Ash to shut up. Ash's response? "Don't let the bed bugs bite!" The way Ash delivers that comeback is hilarious!
On their way to the Pokémon Tower in Lavender Town, Brock accidentally pulls Pikachu's tail, and gets electrocuted and scares Misty. Then Ash says it scared him too, enough to turn him into a ghost, and turns around with his face replaced by a skull. The others are not amused to the point where Pikachu electrocutes him.
When the trio and Pikachu arrive on an island full of turtle Pokémon, Ash and Squirtle examine a Blastoise shell and immediately fall asleep. In an attempt to wake them up, Misty orders Pikachu to thundershock them. Ash and Squirtle are not happy.
Later, when they're saving Team Rocket, Jessie is less than thankful.
Jessie: Just what do you think you're doing?!
Misty: Don't you give us any attitude, we just saved your slimy lives!
James: Well, I'm grateful.
Jessie: They're our mortal enemies! How dare you be grateful they saved your life!
Anytime James calls out Victrebel and ends up getting attacked.
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!
From The Lost Lapras, after Tracey interrupts Team Rocket's menacing abduction of a Lapras because he wants to interview Meowth:
Jessie: Who are you, anyway?
Tracey: Oh, sorry. My name's Tracey, I'm a Pokémon watcher!
Jessie: O-kay, if you're a Pokémon watcher, then you won't mind stepping aside and watching us steal this Lapras.
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!"
In the same episode Team Rocket interrupts Lorelei's lecture and suggest her to try and sell them. As it happens, she already does it.
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.
In The Stun Spore Detour, Jessie is paralyzed and bedridden after getting stunned by a Vileplume, but somehow manages to work up enough energy to return to her hyper violent self and starts stomping James. Then she weakly crawls back into bed.
James as a Moltres. Eric Stuart even commented that his favorite line he did with the show was "I AM A FLAMING MOLTRES!"
In "Moving Pictures", Brock, in response to having to hear a story with Ash, Snap, and Misty from an old lady, said probably one of the funniest and most OOC lines IN THE ENTIRE SERIES.
Snap: We're stuck now.
Ash: She's getting ready to tell her whole life story.
Misty: We'll be here forever...
Brock: I wonder if she has any string cheese.
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 the episode, One Trick Phoney!, where Team Rocket use a Battle Park (which was closed for repairs) to try and steal Pikachu, Ash's Totodile faces off against the park's Charizard, as part of a practice battle. The crowning moment of funny during that battle would have to be when the two Pokemon basically have a Scary Face attack contest, with Jessie and Ash shouting at the two respective Pokemon to make their Scary Face attacks "even scarier!" and "way, way, WAY scarier than that one!", etc., etc... (to the point where the mons are straining their faces, puffing out their chests so that it looks like their lungs are about to burst, and looking slightly constipated, except with their mouths wide open)... until the mons lose balance and fall over backwards. Totodile wins the battle in the end, via a Watergun blast to the Charizard's back, regardless. But either way, Totodile's and the Charizard's "scary" facial expressions were priceless!
James: So who out-scared who?
Meowth: I'm not sure if I'd call that scary, or disturbing...
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.
Love, Petalburg Style is a mix of this, Heartwarming Moment and a bit of a Moment Of Awesome. It seems that throughout the episode, May and Max's dad Norman is having an affair with Nurse Joy and when everyone tries to call him out on it, he's clueless the entire time until they point it out.
Jessie catching Seviper without using a single Pokémon...and succeeding!
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:
Jessie: Do this right Seviper, now go use Sacred Fire! [Seviper does nothing.]
Meowth: Uh oh...
James: I'm not sure Seviper knows how to use that attack...
Jessie: Well, come on! Use Sacred Fire! What are you waiting for?
It gets even more hilarious from there. Upon realising that Seviper can't, in fact, use Ho-Oh's signature move, she immediately tries to get Seviper to use Water Pulse, Blaze Kick, Dragon Claw, Psywave, Luster Purge, and so on. Seviper's embarrassed reactions get more and more ridiculous, ending in a *sweatdrop flood*. Finally, Meowth recommends a Poison Tail attack, which Seviper actually does...only to use it on Jessie, launching her through the roof and out of the contest arena.
The way Corphish defeats Katie's Golduck in the Hoenn League is this and possibly its 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.
In There’s No Place Like Hoenn, May's Torchic is kidnapped by Team Rocket in their latest scheme to capture Pikachu. Ash, Pikachu, May, Norman, Caroline and Max find Team Rocket's balloon and May and Max run to the their balloon, despite Ash's warning not to.
Ash: Not so fast, be careful -!
*May and Max fall into the classic pitfall trap*
'Ash: ...There could be a trap.
*Norman and Caroline start rushing ahead to help them*
Norman: I'm coming!
Caroline: Me too!
Ash: But there might be -!
*Norman and Caroline fall into another pitfall trap*
Ash (facepalm): ...Another trap.
From the same episode, whenever Max forgot Ash's name, calling him "Alf".
Not to mention he keeps bringing up the fact that Ash lost in the second round and Ash points out it was the Victory Tournament.
Probably a case of Off Model, but see the look on Ash's face a few minutes later when Torchic attacks Max. He looks like he's relishing sweet revenge...
Simply the fact that Ash is actually being Genre Savvy about Team Rocket's pitfall traps is hilarious in-and-of-itself! The idea of Ash and his friends have actually used TR's own methods against them is a sporadic, but effective, recurring joke as well..
When Team Rocket attacks Petalburg Gym, Pikachu tries electrocuting Team Rocket but accidentally hits Max instead.
There's also the fact that Torchic attacks Max 4 times. The first 2 times are for Max saying Treecko was cooler while Norman and Caroline don't show any concern for Max. Then when they're fighting Team Rocket again, May tells Torchic to use "Amber" and Max tells her the attack is called "Ember" which Torchic uses on Max. Then May tells Torchic to use Peck and Torchic starts pecking Max.
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!
*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 and Pikachu as its targets!
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.
Jessie: Prepare for trouble, we've shuffled the deck!
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...
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...
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 story, or the guy reading it?
Harley and Jessie's contest in A Hurdle for Squirtle!. Harley uses his signature Ariados, while Jessie uses Wobbuffet. With Harley Genre Savvy enough to not try to attack Wobbuffet, due to Counter and Mirror Coat, and Wobbuffet not being able to attack at all, we have both of them getting yellow cards and then the contest turning into an insult match. And then Ariados and Harley end up dancing while twirling around Wobbuffet with String Shot. "A one-y and a two-y and a buck-o my shoe!"
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!
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!
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.
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 Off The Unbeaten Path, Jessie and Meowth are sent blasting off with their traditional cry. James meanwhile, off trying to win a contest fairly, overhears them, leading to this remark.
James: I thought I just heard someone say 'We're blasting off again' but we copyrighted that!
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.
While trying to master Aerial Ace in Lilycove City, Swellow ends up falling down and gets its beak stuck in the ground. In the next episode, Swellow misses due to not paying attention and when it finally succeeds, it accidentally hits Team Rocket, causing them to blast off.
During the Lilycove Contest, Jessie has Chimecho use Heal Bell, soothing the audience, but finds it boring and has Chimecho use Astonish, much to everyone's dismay, and even affects Ash, Pikachu, and Swellow who are outside. Of special note, it somehow affects Meowth and Swellow despite normal types being immune to ghost attacks.
In the same contest, Meowth's deadpan facial expression at James' horrified reactions during Chimecho's battle against May's Combusken.
May: Use Fire Spin!
James: She's using fire?!
In Having a Wailord of a Time, Ash, Max, and Pikachu are supposed to be taking care of a Treecko, Mudkip, and Torchic. The Torchic attacks all the other Pokémon, runs away, and evolves into Combusken. Max suggests that they switch the Combusken with May's Torchic and imagine the result.
Fantasy Max: Congratulations, May! Your Torchic evolved into Combusken!
Fantasy May: Who are you kidding?! Do you think I'm some kind of idiot?! What have you 2 done with my Torhic?!
Ash: That plan...
Max: You're right, she'll see right through that one.
They still use May's Torchic in place of the Combusken and try persuading the new trainer to pick Treecko or Mudkip instead.
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!
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!
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!
There's a reason he's an Ensemble Darkhorse among the Sinnoh Gym Leaders, despite having (alongside Crasher Wake) the smallest episode count of all eight of them.
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!
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.
It's also hilarious because when they're all on the Rocket (just after Happiny has restored the guys to their senses), Happiny and Togepi have the baby Pokémon equivalent to a cat-fight (while everyone else is trying to get control of the rocket).
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.
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.
Earlier, Meowth tries to convince Jessie and James to get Glameow from the trainer using a hastily-created Giovanni fantasy. Even they immediately point out the holes in it.
Dawn's Early Night: Ash's reaction to Nando telling him 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.
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.
Once Team Rocket's been taken care of, Ash asks for the rest of his Pokémon, cue Glalie freezing him and Torkoal thawing him out.
Poor Bulbasaur. The only one of the originals to appear, made worse since it involves him getting assaulted 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:
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!
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!"
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!
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.
Even funnier when it was the fact that: 1) Dawn could tell what Gible was about to do a mile away and 2) the meteor defies physics by traversing a cave system to find the penguin.
Minor one, but seeing Team Rocket root for Ash during the Sinnoh League Victors season was worth a few chuckles.
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!
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!
Dawn getting lost on her way to Professor Rowan's lab in the first episode of Pokémon DP. "Not there!...Wrong way!...I want my mom!"
In the end of Double-Time Battle Training, Jessie makes Team Rocket blast off by her two Pokémon (Yanmega and Wobbuffet).
At the beginning of "Noodles, Roamin' Off!", Ash and friends are walking along a road when their usual assailants ambush them. Their response? "Oh, it's just Team Rocket." Ash says he's too busy to battle and tells Pikachu to blast them off with a quick Thunderbolt. He does.
A wild Phione uses Supersonic on Meowth in Hold the Phione! The effect is priceless.
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"!
Meowth claims to have been mistreated by Jessie and James, including one particularly priceless flashback line. "I didn't tell you to buy bread, I told you to buy bread!"
Steamboat Willies: the Pokémon start a band. Epic Fail ensues.
Ash and his friends mimicking Team Rocket's motto in "The Keystone Pops!"
Paul trying to catch a Fearow in "A Maze-ing Race!", only to be constantly interrupted by Ash and his friends, who have been separated from and are looking for one another.
A Gruff Act to Follow!: Dawn's reactions to Paul not remembering who she is. The first time is accompanied by a volcano erupting in the background. The second time? Not only has Dawn turned bright red and has huge glowing red eyes, but the background is of the sun splitting into quarters. Brock has to run in and restrain a kicking and screaming Dawn.
Dawn: Wha-what's wrong?
Paul: What's wrong? Who are you?
Dawn: Excuse ME, your rudeness, but we've met once before, the name's Dawn!
Anytime Brock flirts with a girl and receives a Poison Jab from Croagunk. In one episode, Pikachu and Piplup attack him and drag him away.
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.
In the ninth episode of Best Wishes (The Bloom is on Axew!), 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.
Cilan then dubs the attack "Dragon Sneeze." Iris is not amused.
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.
Scraggy: Hatched to be Wild! Ash's Scraggy finally hatches from its egg. Later, when Ash's other Pokémon try to greet him, he tries to fight him all. Pidove gets freaked out by Scraggy's Headbutt. Oshawott gets so mad he has to be pulled off Scraggy. Then he tries taking on Tepig and eventually Snivy, who casually jumps off a rock so Scraggy crashes into it and then casually holding Scraggy off with her vines. And then he headbutts Ash.
A wild Minccino using Tickle on Bianca's Pignite in BW013 (Minccino- Neat and Tidy!). 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.
How the Minccino was caught can also qualify. Once Bianca is ready to catch him, she pulls out a very dirty Poke Ball, but takes so much time doing so that he gets away. Howver, out of instinct, he goes over to clean the Poke Ball, accidentally getting caught in the process.
In the The Battle Club and Tepig's Choice, 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.
Scare at Litwick Mansion!: Cilan screaming like a little girl. That. Is. All.
Burgundy's Imagine Spot of Evil Cilan in A Connoisseur's Revenge, 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.
And gets vine-whipped in the tongue for her trouble.
All of the Pokemon's abusing her is pretty funny but Pikachu takes the cake. You can mock his trainer and insult his friends, but the moment you declare he isn't cute is the moment where he deals out 10000 volts of electricity.
Iris and Georgia's interactions as rivals. It's basically a Cat Fight without any actual fighting, and it's hilarious.
In Reunion Battles in Nimbasa, 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.
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.
Later in the episode, Emolga pulls a Wounded Gazelle Gambit by explaining how a trio of Watchog tormented her...in a little scene illustrated with paper cutouts. It's so cute it's funny.
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!
Oshawott's Lost Scalchop!: Oshawott thinks he finds his scalchop and puts it on his chest. It's a Joltik. The little critter is not happy about this.
Sawk using Bulk Up in The Club Battle Hearts of Fury: Emolga vs. Sawk!, where he strikes some of the most over-the-top and manly poses you can think of. Like this.◊
More funny is that he does that EVERY TIME he uses Bulk Up. And Bianca goes nuts.
In Club Battle Finale: A Hero's Outcome, 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 in reference to the Pokémon Musical subplot. 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 "Evaluation Time" duet. Enough said.
In Dazzling the Nimbasa Gym, 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..."
Put that into perspective: He forgot his own Pokémon's sex.
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.
Basically everything Meowth does, falling asleep and messing with Ash (not on purpose) and getting woken up by being spiced. The Dream Thief is hilarious in the Japanese original with his absolutely ridiculous Gratuitous French which completely steals the spotlight
Cilan and Stephan cosplaying as Elesa and Nurse Joy, respectively. Cilan can pull it off. Mostly.
Made funnier by the fact he lost simply because he was too into the role and creeped the judge out.
Plus the judge is a fan of Elesa, making Cilan's crushed reaction to knowing he probably couldn't have succeeded all the more priceless.
The mere sight of Tepig and Oshawott in afro wigs in the episode "Baffling the Bouffalant" is enough to make people laugh BEFORE the episode aired.
Snivy absolutely refusing one also warrants a mention.
It should be noted that the dub of the episode seems to go out of their way not to say the word "afro". The fact that at least one background track in the episode is noticeably Funkier than you'd expect for the series lets you know that yes, the dubbers know full well that they're not fooling anyone.
In that same arc, Cilan's Evaluation Time getting stopped by Stephan's Sawk's karate chop and its followed up by Pansage's dodge failing against Sawk's low sweep. Followed by Cilan's shocked look and then PANSAGE GETS SMACKED RIGHT INTO CILAN!! The funniest part is the slapstick sound effect that further emphasizes how much Cilan got curb-stomped. This is then followed by the announcer getting Stephan's entire name wrong.
Bianca's obsession with muscles. That is all.
This exchange in Battling the Leaf Thieves (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)
From another movie-making episode, they decide to spoof the famous MGM logo...and they had to use a Zorua instead of a lion analogue! What.
From Crisis at Ferroseed Research, after the whole moss issue is resolved, Ash thought it would be a good idea to have Pikachu unleash all the electricity stored in his body. So Pikachu lets it out, but the electricity comes back and almost hits Oshawott. Oshawott blocks the electricity with its scalchop but then it hits Ash, Iris, Cilan and Georgia. When Oshawott turns around to see what happens, he puts his scalchop down and gets electrocuted too.
From Piplup, Pansage, and a Meeting of the Times, Dawn's reaction to Cilan's "EVALUATION TIME!" is priceless.
In the same episode, after the big finish between Piplup and Pansage's battle, Meloetta comes up to dance with Piplup. Oshawott comes out of his Pokeball in a jealous fit and Piplup just reacts with an awesome "u mad bro?" face.
Additionally, while Dawn, Iris, and Ash are giving their reactions to Cilan's Evaluation Time speech, Cynthia just sits there and still watches without being phased or thrown off by Cilan. Either she is a master of being stoic or has a Weirdness Censor.
In "Clash Of The Connoisseurs", Cilan's Crustle accidentally sends Burgundy "blasting off" with one of its attacks. At that point, Ash (elsewhere in the general area) looks up and notes that that sounded oddly familiar...
Scrafty's method of kidnapping Axew in Meowth's Scrafty Tactics — it shoves Axew into its pants.
All for the Love of Meloetta!: The gang and Cynthia are heading out when suddenly, the music turns tense, she mutters "wait just a minute..." and the scene darkens and goes to a close-up of Cynthia's eyes, putting everyone on edge. After about three seconds, she finally figures out what flavor of Bearticone she wants. Everyone else pretty much collapses.
In Lost At The League, Pikachu's reaction to Oshawott stealing the apples the Trubbish were going to eat. He pulls this blank face as he mutters "Pika Pika" stoically as if to say "Oshawott...you're an idiot." And Emolga doing the same made it even funnier.
In The Fires of a Red-Hot Reunion!, Iris wonders why her Dragonite's Dragon Rush didn't do more against Ash's Charizard, as it is a Dragon Type. This is quickly followed by three beat reactions from Ash, Cilan and Pikachu. Charizard, however, has a completely shocked WTF face complete with sweatdrop, while Iris's Dragonite just has a "Really? -_-" look.
N was also included in on the reactions. Epic Fail indeed, Iris.
Then, after Oshawott wins the battle against Caesar and is crowned the winner, Oshawott goes all heart-eyed again as Ash says a tearful farewell to Oshawott. However, Osharina rejects Oshawott in the favor of Caesar, who also had a love interest in Osharina. Oshawott's reaction is PRICELESS! Heck, even Oshawott's scalchop breaking in half (representing his broken heart) made it much funnier!
In Team Plasma's Pokémon Manipulation!, Team Plasma grunts are at the white ruins, observing the excavation. They report that nothing has been uncovered by Cedric Juniper's excavation team. Cut to Cedric Juniper...
Cedric: Look! The discovery of the century!
Researcher 1: Huh?
Researcher 2: You've done it Professor Juniper!
Cedric: Hasn't happened yet. Back to work!
The Best Wishes Decolora Adventure! ending theme ends with an impressive shot of all of Ash's friends and rivals holding hands with one another. Including Paul. Paul. Holding. Hands.
Cilan And The Case Of The Purrloin Witness has Character Of The Day Mr. Shaw make a vow to get the Liepard's Eye jewel and makes an evil laugh though he's not evil. Response? Watchhog slams the door in his face, and it's like it's telling him "Shut up!"
In The Island of Illusions, Ash runs Zoroark!Nurse Joy and Audino ragged by asking where each one is. So they keep running back and forth and back and forth until they get exhausted.
The first act of The Path That Leads To Goodbye! is presented by Cilan as a How We Got Here flashback. At the start of the second act, Team Rocket is preparing to ambush the twerps, and Meowth gets his own How We Got Here flashback... to a ten-second scene of them deciding to ambush them. Jessie even calls out his bizarre narration by the end.
Pignite in The Journalist From Another Region beats down several Pokemon in the tournament including a Slaking...but he didn't need to beat it up. Instead, he beat it because Slaking was, well, slacking off!
It seems Bonnie is the new Brock of this season- every time a pretty girl shows up, she gets down on one knee and proposes they marry...her brother.
And to mirror Brock getting dragged away by the ear, Bonnie gets dragged away by Clemont's mechanical Aipom arm.
In XY010, James's rambling during the Cold Opening gets cut off by the opening theme.
The "overuse" of the word Mega during that segment.
In the same episode, Bonnie and Serena's imitation of Team Rocket's introduction. Later, Team Rocket says it themselves, only to find Ash and Clemont weren't listening and trying to get Bonnie, Professor Sycamore, and Serena untied the whole time.
When Jessie and James tie up the girls, Bonnie orders Dedenne to attack, who's crawled into her backpack to take a nap.
Serena getting bombarded by Fletchling just like the games. However, unlike the games, this is much funnier.
It's early days, but it's already been well established that Clemontic Gears rarely last more than a few minutesbefore blowing up in everyone's faces and giving the human characters afros. The aftermath is always hilarious, but especially with the Sticky Web cannon, which gave all the Pokémon that were currently out afros as well. Including Fletchling. Pikachu even gets one on his tail!