The journey is not all fun and games...
As a Moments subpage, all spoilers are unmarked as per policy. You Have Been Warned.
- The extended sequence showing the death of Blue's Raticate. It starts out as a freak accident when Red's Nidoking accidentally throws him into the sea while he's poisoned in the spur of their battle. The Pokémon is then shown slowly drowning while Blue is frantically calling for help and trying to send him back into his Pokéball, but can't because he's out of reach. There's then a brief Hope Spot when Red warns the captain and his crew, and they manage to retrieve Raticate... But they fail to revive him. Red and Blue are understandably devasted, and we're treated to a shot of Raticate's empty Pokéball. The sequence ends with Blue heartbroken, and Red crying alone in a corner of the ship. Made even worst by the fact that it was shown a few times that Rattata/Raticate was the Pokémon with whom Blue was the closest, perhaps even more than with his starter. The entire scene is highlighted by a sad reprise of the SS Anne theme.
- Red's battle against Surge soon after. To take on the Gym Leader's fast Electric types and with his Geodude down Red sends in Nidoking... And recalls him immediately as him slapping Surge's Pikachu gives him a flashback to Raticate's last fight. Eventually however he's forced to send Nidoking back in to deal with Surge's Raichu... And as Nidoking wins Red starts breaking down and the sequence is juxtaposed to Surge's flashback of the war between Kanto and Hoenn. It concludes with Surge giving Red the Thunderbadge and then hugging him, just as he had to do after the war when he had to tell the widow of a fellow soldier that her husband had died.
- Red's Nidoking being boxed, though it also doubles as a Heartwarming moment. Red finds himself unable to use his Nidoking anymore due to the trauma related to Blue's Raticate's death, and chooses to box Nidoking. Nidoking understands Red's reason and dries his tear, leading the two of them to share a hug. We're then treated to a good-bye montage showing the key moments of their shared journey, before Nidoking presses himself the button of his Pokéball to be left with Oak.
- Giovanni's backstory. He started out as a formidable trainer - enough to come second at the first Pokemon League, only beaten by Oak -, a capable gym leader, and a honest researcher with some odd theories, such as that Gengar and Clefable may be related, Pokemon may all descend from the mystery Pokemon that he saw and managed to get a strand of fur from, or that one could induce a Pokemon to evolve through radio signals... But years of having people, fellow researchers, and even his friends literally laugh at his theories while having to watch Oak being celebrated for the first incarnation of the Pokedex (then a simple paperback encyclopedia) and the far less intelligent Bruno progress to the Elite Four in his place drove him to first steal a rare sample of what he identified as Mew's DNA to try and get Oak's help. When the latter kicked him out of his lab in anger for the theft, Giovanni went and founded Team Rocket to get the funds and expertise needed to prove he was right at least about Mew by cloning them... And then Mewtwo blew up Pokemon Mansion, and he lost his daughter in the chaos.
- Giovanni's moniker of "The Self-Proclaimed Strongest Trainer" is hinted to be mockery given to him due considering himself stronger than Bruno.
- Here's a Fridge one. The identity of Giovanni's daughter? All but stated to be Mars. Meaning she grew up to work for (and implied to grow a crush on) Cyrus.
- Eventually he tracks Mewtwo down and tries to capture them... And Mewtwo bulldozes through his entire team due their overwhelming power and being a Psychic type faced with part-Poison types, even gouging out one of Giovanni's Nidoking's eyes. At which point Giovanni snaps and punches Mewtwo in the face... Only to be contemptuously swatted away.
- Leaf's backstory. She was once an orphan living in the Sevii islands, though in an Orphanage of Love... Then Archer and Team Rocket arrived and took over the islands, devastated the orphanage, and conscripted her and the other children into Team Rocket. She was a Rocket grunt for years until she managed to stowaway on a boat bringing captured Pokemon on the mainland, boat she jumped off as soon as they were close to the mainland near Pallet Town. Her goal is to defeat Team Rocket and free the Sevii Islands... But she's got no money and no Pokemon, hence her trying to steal Oak's Bulbasaur.
- Leaf's initial Little Black Dress is implied to be her Team Rocket uniform, modified on the boat. She has literally nothing else until Red and Professor Oak take her in after the attempted theft of Bulbasaur.
- After Red defeats Team Rocket in the Pokemon Tower, he has a brief encounter with Raticate's spirit. While the moment is also heartwarming, since Raticate tells Red that it knows it was an accident and it doesn't blame Red, the sight of Raticate's spirit moving on alongside the Marowak mother can still get one teary-eyed.
- The outcome of the Silph Arc is actually rather morose for the two main characters, which creates a huge contrast with the rest of Kanto who's celebrating Team Rocket's defeat.
- Red is shown to be extremely uncomfortable with this newfound fame he didn't want. He'd rather be left alone, but wherever he goes, people or journalists are waiting for him. His inability to find peace and tranquility actually brings him to tears.
- Blue resents Red for his newfound fame, since he also took part in fighting Team Rocket but didn't receive any glory contrary to Red, and especially because he thinks he has to live up to his grandfather's and his sister's accomplishments. It leads to the birth of his toxic competitive mindset, which culminates in a sad scene during which he dismisses his very first partners (his starter, his Pidgey, and his beloved departed Rattata) as too weak.
- After Silph Co. Oak and Agatha tell Red about their past with Giovanni and how he was driven to villainy by his obsession with a non-existing Pokemon... And then Red pulls out that very Pokemon, Mew, making them realize that they have contributed to Giovanni's fall into villainy.
- Giovanni is a ruthless and cruel mafioso, but the scene showing him completely losing it after he failed to achieve his ambition (literally right after he thought he had succeded) and his son Silver renounced him simply screams Cry for the Devil.
- Sabrina's past. There's a good reason she's so cold in the present... To give a few details, it involves her working in a Circus of Fear, under the watch of an abusive ringmaster who used a whip to keep her in line. A whip like the one Sabrina carries in the present and uses to give orders to her Pokémon.
- We later learn that when she faced Blue, she had what appears to have been a panic attack after he defeated her. He responded by pointing and laughing. Sabrina ends up envisioning this as her back in her circus days being laughed at by an entire audience of Blues.
- During the Gym Battle with Red, Giovanni's look of shock when his opponent sends in Mew, nailing down how his years of villainy were All for Nothing.
- After the Gym Battle Giovanni disbands Team Rocket and asks Red to meet again in better circumstances one day. It then cuts to the party for Red's 25th birthday... And it appears that neither Red nor Silver have seen Giovanni ever since.
- The sequel series reveals that Silver did briefly see Giovanni again during Johto, but it was only because Giovanni wanted to remind the Rockets of the promise he made to Red. After seeing Silver reject Team Rocket's goals, Giovanni left, never to be seen again.
- Blue's entire arc post-Silph Co, which is Dude, Where's My Respect? made manifest. Despite his jerkass stat levelling up to his game-canon levels, you kinda want to give him a hug. To wit:
- Blue's desperation to prove his worth is reaching tragic levels in Episode 42. While he keeps his cocky demeanour in public, it's pretty clear he's on the verge of a breakdown. When Red defeats him with Legendaries, he scoffs at his rival's victory, but stops hiding his tears of frustration when Red can't see him. At the end of the episode, Blue tearfully prays for victory.
- What makes Blue's breakdown even more tragic is that Oak and Daisy are actually fully supportive. When they see him unhappy after he became the new Master, they are actively trying to help him overcome his insecurities. However, because of Blue's inferiority complex, they have a hard time connecting with him.
- Blue's unhinged look during his title defense against Red, showing that all the humiliations are about to turn him to villainy as it had happened to Giovanni. Thankfully, Oak arrived in time to calm him down and declare how proud of him he was, preventing that tragedy from repeating.
