The finale of Season 1. Steven is down to his last Pokemon, Metagross. Ruby commands Absol to use Perish Song, as he knows that none of his remaining Pokemon can take Metagross one on one. On that same turn Absol is KO'd by a Meteor Mash, 3 Perish Song counters remaining. Ruby follows with Katie, and she is easily disposed by an Earthquake from Metagross, 2 Perish Song counters remaining. Now Ruby is down to his last Pokemon, Sceptile, and as a Hope Spot arrives he is reminded of all the Pokemon he lost to get there, and that everything was for a reason; he just had to survive until the end of the turn for the Perish Song to take effect.
Then Metagross used Hyper Beam. And everything faded to white.
Those same tears become bitter when N walks up and hits Ruby with a simple truth, that in turn potentially reopens every single tearjerker death in the past. "Yes, it is sad... But remember... They wouldn't have died... if you hadn't caught them."
Emerald Comic - A Shoeless Adventure:
Chapters 10 and 11. Each Pokémon gets a well-developed character, and when they die, it hits hard.
Freddy's Nuzlocke Adventures:
Towards the end of his first run comes this. The music does not help.
Rikishi'sHeroic Sacrifice during the Champion battle. Complete with a flashback.
In Landwalker's Yellow run, the death of Blue's Raticate, trampled by evacuees when the SS Anne burns/sinks. Complete with shots of Blue desperately screaming and searching for it.
Also, Lun the Diglett's death.
Amy's death to a self-destructing Koffing. Red's reaction after all of it concludes does not help.
The battle against Lorelei has a wham moment that hits hard. A mere one episode after joining, Vinny the Magneton- already shaping up to be a fan favorite- is killed by Lapras' critical Surf. Good night, sweet prince.
Petty's formspring makes an earlier event much harsher. Remember when James tossed Gary out of the S.S.Anne? His Raticate died saving him
The final battle with Gary◊. Nadine going down after a stray Future Sight gave Gary's Charizard enough of an edge to finish her off. Made worse in the comments for the page, where Petty describes how she simply didn't have any choice but to let Nadine die due to Charizard's speed outclassing anything else on her team.
On top of this, immediately following the battle, Oak arrives and coldly shuts down Gary's protests, driving home the very same favoritism towards Locke that messed up Gary so badly in the first place.
Gary: But Gramps! I WON! I was Champion! I was actually SOMETHING until she—
Oak: GARY. Go home. (He then proudly embraces Locke, ignoring and turning his back on his grandson) Come with me, Locke. We'll enter you into the Hall of Champions.
A rare tearjerker induced by a happy scene. Spuds and Barb adopt an egg.
And the next chapter focuses solely on the aftermath to show how major it was. Zach and Jojo's evolutions, even though it is their final forms, do not change the tone slightly.
Jordan even got "Saddest Death" for the 2013 Nuzlocke Awards on the Nuzlocke forums. That is how much of a Tear Jerker it was.
wizard898's Moemon: Hard Mode:
A heartwarming picnic takes on a bittersweet air when Saya goes to help clean off her master's mouth and he rebuffs her.
Ruru'sHeroic Sacrifice, especially as her Static kicking in proves key to their victory. The expression poor Chu makes as it sinks in just makes it worse.
Chapter 21: Volt's death. Just to see a poor sweet little girl implied to be beaten to death...that just sucks. Doubles as a You Bastard moment for Team Aqua.
22 rubs salt in the wound, as Tooh blames their trainer for what happened, calling him weak and refusing to follow him any longer. Umpa joins her.
Nonparael's Nuzlocke Runs:
The three-part Episode 10 of the Moemon LG run, combines this with Wham Episode: first, Gale Oak reveals he knows what the heroine is trying to accomplish, calling her cause 'crazy'. Then he forces Sienna's charmander friend Allie to kill Sienna, followed up by Tia's death. The heroine reveals herself as a moemon Weepingbell, but Gale has her pokeball, and Nail performs a Heroic Sacrifice. To rub it all in, Gale mocks her afterwards.