Victory Doesn't Feel Very Good
Boss fights are supposed to be a cause for celebration, so why is it that these 20 games made us feel awful when the credits finally rolled? Oh, right, because the enemy across from us is an old friend, a family member, or someone whose “evil” plan was actually disturbingly reasonable. We’re here to revisit the battles that made hacking at that health bar almost cruel.
1. The Boss — Metal Gear Solid 3: Snake Eater
Snake spends much of Metal Gear Solid 3 hunting the woman who trained him, which is bad enough until you discover that The Boss's apparent betrayal was ordered. She knowingly accepts that history will remember her as a traitor so Snake can complete his assignment, and pulling the trigger doesn't feel like winning at all.
2. Great Grey Wolf Sif — Dark Souls
Sif isn't plotting the destruction of Lordran when you find the giant wolf guarding Artorias's grave. The furry creature is just protecting its master's resting place and, if you've rescued Sif earlier, it even recognizes you before reluctantly taking up Artorias's sword. Things only get worse when an injured Sif starts limping during the fight.
3. Maiden Astraea — Demon's Souls
Most Archdemons make it easy to feel heroic about ending them—but not Maiden Astraea. She spends her time comforting abandoned, diseased people. She also became a demon after concluding that the valley's rejects needed compassion more than they needed the God who forgot them. By the time she asks what you want, we just feel terrible.
4. Xion — Kingdom Hearts 358/2 Days
Roxas and Xion spend much of the game becoming close friends before Organization XIII's plans make their coexistence impossible. Knowing Roxas will disappear if she sticks around, Xion forces him into a battle that ends with her destruction. We’re then forced to watch Roxas struggle to remember his dying friend afterward.
5. Braska's Final Aeon — Final Fantasy X
The enormous creature at the end of Final Fantasy X isn't another monster. Nope, Tidus knows him as Jecht, his estranged father. Jecht became Lord Braska's Final Aeon years earlier and ultimately became Sin, leaving Tidus with the miserable responsibility of putting him down. Sure enough, their complicated relationship begins to soften just when you’re supposed to attack him.
6. Akira Nishikiyama — Yakuza Kiwami
Kiryu and Nishikiyama grew up together! They were in an orphanage and regarded each other as brothers! Ten years apart leave Nishikiyama bitter, ruthless, and consumed by everything that happened while Kiryu was in prison, eventually putting the two childhood friends on opposite sides of the coin. It’s like the fox and the hound all over again.
7. Lord Shimura — Ghost of Tsushima
You know, Lord Shimura isn't just Jin Sakai's superior because he raised him. He effectively became his dad, which is what makes their differing beliefs about honor so upsetting to see. It also forces them into a deeply personal duel after the Mongol invasion has already cost them both so much. It’s just not something you want to play through, and yet, here we are.
8. Takuto Maruki — Persona 5 Royal
Maruki wants to rewrite reality so people no longer have to endure the pain that shaped their lives. His solution? Remove people's ability to determine their own futures. Yeah, well, Persona 5 Royal makes his ideal world pleasant enough that rejecting it isn't an easy moral decision. Fighting your former counselor while he insists he can make everyone happy is far sadder than other confrontations.
9. The Shadowlord — NieR Replicant
NieR wastes a lot of time encouraging you to hate the Shadowlord for taking Yonah—then reveals how misguided you’ve actually been. The Shadowlord is fighting for his own Yonah and has spent a ton of time waiting for the chance to reunite with her. Once those details kick in, killing him is a lot less heroic.
10. Handler Walter — Armored Core VI: Fires Of Rubicon
Walter initially treats C4-621 as an asset, but his relationship slowly develops into something weirdly paternal. In one ending, Arquebus captures and reconditions Walter before sending him to fight the person he spent the entire game guiding. His brief moments of returning awareness make things that much worse to stomach.
11. Emma, the Gentle Blade — Sekiro: Shadows Die Twice
Most players know Emma as the physician who assists Wolf, which makes the Shura route's consequences especially ugly. After Wolf abandons Kuro and sides with Owl, Emma draws her sword, realizing the man she helped is now a genuine threat. Winning means murdering one of your closest allies, so hooray.
12. The Hollow Knight — Hollow Knight
The creature sealed inside the Black Egg was never the mastermind behind Hallownest's suffering. It was created as a vessel meant to contain the Infection. So, seeing the Hollow Knight stab itself makes the encounter less like defeating a boss and more like ending something's prolonged misery.
13. The Masked Man — Mother 3
A lot of time goes into Lucas grieving Claus, but near the end, the mysterious Masked Man is revealed to be none other than the twin himself. Of course, he’s rebuilt and controlled by Porky's forces, so little of his former personality is in there, but that only makes it worse. The fight is particularly devastating once Lucas realizes he isn't trying to defeat a stranger at all.
14. Doctor Octopus — Marvel's Spider-Man
Say what you want about Peter Parker’s enemies, but we’ve always had a soft spot for Doc Oc. Peter himself admires Otto as a mentor and genuinely believes his work can improve people's lives. But Otto's decline, resentment toward Norman, and growing dependence on his arms transform that relationship into something darker. It’s not like fighting a villain—it’s like fighting a friend.
15. Bode Akuna — Star Wars Jedi: Survivor
Bode enters Jedi: Survivor as Cal Kestis's new companion, which makes his eventual betrayal all the more painful. He turns against Cal mainly because he's terrified of losing Kata. He’s also convinced that keeping Tanalorr hidden is the only way to protect her. His actions are increasingly indefensible, but even so, hearing Kata watch her father die carries plenty of damage.
16. AI Professor Sada or Turo — Pokémon Scarlet & Violet
Pokémon Scarlet and Violet eventually reveal that the professor guiding you through Area Zero is actually an AI created by the real Professor Sada or Turo. It understands the dangers of the professor's time machine and actively helps you shut it down, only for its programming to force it into battling you when you try. It’s messed up to defeat an opponent that's effectively begging you to stop the plan it has been programmed to defend.
17. Emet-Selch — Final Fantasy XIV: Shadowbringers
Emet-Selch commits some pretty heinous stuff while trying to restore the civilization he lost. Shadowbringers gives you enough time with him to understand his grief, even as it makes clear that restoring his world would mean sacrificing countless lives in yours. Either way, his final request doesn't produce the celebration we were hoping for.
Enrique Guzmán Egas on Unsplash
18. Asgore — Undertale
Asgore has every reason to look like Undertale's greatest villain. Then you meet him, and he’s just a lonely, grieving king who regrets the promise he made. In an especially grim twist, he even destroys the Mercy button before the fight, refusing you the right to spare him.
CERO, Nintendo, 8-4, Ltd, Temmie Chang and Toby Fox on Wikimedia
19. Ganondorf — The Legend of Zelda: The Wind Waker
The Wind Waker gives Ganondorf more introspection than many Zelda games, and we’re not exactly grateful. His envy turns into destructive ambition, so the game doesn't excuse what he did, but it does give a recognizable motive to his obsession. Stabbing him just feels necessary, even if his quiet acceptance makes the moment unexpectedly bleak.
20. Vergil — Devil May Cry 3
Dante and Vergil clash over their radically different responses to the trauma that followed their mother's murder. Vergil pursues demonic power; Dante accepts his responsibility toward humanity. The whole thing ends in a blowout with Vergil choosing to fall into the demon world rather than take Dante's hand, and we still haven’t recovered.
