- Angst? What Angst?: Zig-Zagged with Ash in regards to his mother. Some episodes, he's shown to be distraught by the fact that is mother doesn't love him. Other times, he seems ether perfectly okay with it or just completely oblivious about the whole situation.
- Crosses the Line Twice: Pretty much everything Pikachu, Brock and Ash say or do.
- Designated Hero: Almost every episode, Ash actually doesn't do anything and causes destruction without getting called out for it by anyone except Misty. Still doesn't make it any less funny.
- "Funny Aneurysm" Moment / Harsher in Hindsight: After the accusations of emotional abuse and manipulation by 1KidsEntertainment and the confirmation of such being cited as the reason for his retirement, most moments involving Ash become much harder to swallow.
- The Episode 7 "Derub", in which the three main voice actors trade roles and 1Kids takes on the lines of Memetic Molester Brock, become almost terrifying.
- Hilarious in Hindsight: Vaporeon is basically treated as a Butt-Monkey in Episode 19 (even its owner doesn't want it!) Two years later, Vaporeon is one of the absolute best Pokemon in Pokemon GO (at least before the first patch.)
- Misty is ostracized by her family for her interest in fire types. In Twitch Plays Pokémon HeartGold, the Gym Leader types are randomized and Misty gets Fire type.
- Jerkass Woobie: Arguably, all the main characters count.
Keith: Those Goldeen crackers sure were good! Now for the main course: Horsea Raddish! Haaa...(meekly) I miss pizza...
- Ash has an incredibly abusive mother who kicked him out when he was ten years old.
- Misty's family disowned her because she liked fire type Pokemon. Not to mention the fact that Ash and Brock annoy her endlessly and that nobody ever listens to her. Like, ever.
- Brock's father also disowned him due to his obsession with breeding.
- Pikachu is the second most frequent victim (after Misty) of Ash's utter stupidity.
- Tracey grew up in a nudist colony that was woefully unprepared for their first ever recorded snowfall, and every single member of his village died except for him (including his parents, who passed away right in front of him). It eventually led him to make a deal with the devil (i.e. wear clothes) in order to survive.
- The ending to episode 24 seems to imply that Keith and his Farfetch'd are homeless and starving, hence why they steal and eat other people's Pokemon.
- The Scrappy: Barbara for her absolutely annoying voice. She is also considered this In-Universe by Misty.
- Lampshaded when the team released an "improved" version of that episode in which all Barbara's lines were replaced by silence.
- Parodied in Episode 15: the canon version of Max is considered this by a good portion of the fandom, so everyone in the episode (except Misty and Tracey) treats him with disdain.
- The Woobie: Mikey from Ep 19. After Eevee Headbutts Team Rocket out of the way, Mikey chooses to keep Eevee like it is. Later that night, Eevee accidentally evolves into Umbreon, and Mikey's hair and pants were forcibly altered accordingly by his three Jerkass brothers. The pants won many awards, but Mikey is so fed up with their shit that he outright murders all three of them.
YMMV / Pokémon The 'Bridged Series