Completionist's Nightmares

Obsessive amounts of grinding, buggy/annoying achievements, insane amount of minimum playthroughs required, incredibly difficult to do, Etc.
TL;DR - Games with achievements that are actively annoying to get to the point they can ruin (or enhance) the experience if you're going for them.

Black Mesa
Black Mesa
Purple Hat achievement.
The problem with it is the weird physics it has and that it rolls.
Classic NES Series: The Legend of Zelda
Classic NES Series: The Legend of Zelda
RetroAchievements - No death no quit-out achievement.
DreadEye VR
DreadEye VR
Game forces you to have a buzzing phone during your entire playthrough, buy another of the developer's games, not allowing you to reset when the game has janky physics
Final Fantasy: 20th Anniversary Edition
Final Fantasy: 20th Anniversary Edition
RetroAchievements - There's a secret minigame of a "15 Sliding Block Puzzle" (4x4) with 4 achievements based on beating it, each with less and less time for you to beat it. All the other versions of FFI don't have this achievement (or if they do, it's just beating it once) but the PSP version has one for beating it in less than 30 seconds, less than 1 minute or less than 2. Even when doing it with a solver and pausing and unpausing, I barely reached 26 seconds because the RNG of the puzzle was in my favor.

Genji Armor Achievement; Rare drop (1/20) from a rare monster (1/64 chance to appear). Multiple hours of grinding required if not lucky.
Hotline Miami 2: Wrong Number
Hotline Miami 2: Wrong Number
Genocide achievement requiring 50K kills.
The fastest way to grind this achievement takes around 2.5 hours~ by doing an exploit.
Custom levels do not count towards the achievement either.
Jump King
Jump King
An already hard game that requires you to handicap yourself to get all the achievements. Fun, but a miserable experience.
King's Field
King's Field
RetroAchievements - No death no save achievement on a 40h~ish hour game. Incredibly painful to do without speedrunning glitches.
King's Field
King's Field
RetroAchievements - No death no save achievement on a 40h~ish hour game. Incredibly painful to do without speedrunning glitches.
King's Field II
King's Field II
RetroAchievements - No death no save achievement on a 40h~ish hour game. Incredibly painful to do without speedrunning glitches.
The Legend of Zelda
The Legend of Zelda
RetroAchievements - No death no quit-out achievement.
Metroid: Zero Mission
Metroid: Zero Mission
(RetroAchievements) - Set requires you to straight up use incredibly tight speedrunning tricks to sequence break the game.
Monster Hunter: World
Monster Hunter: World
Achievements require to constantly reload big areas with big loading zones that have 1% chance to spawn. Others ask you to stay in the level for 8+ hours before you can even attempt to get them, and there's a chance for it too.
Mortal Shell: The Virtuous Cycle
Mortal Shell: The Virtuous Cycle
Requires 50 hours of grinding to get all achievements in the DLC.
Super Mario Bros.
Super Mario Bros.
RetroAchievements - Pacifist and no death achievements.
Ubermosh
Ubermosh
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh: Black
Ubermosh: Black
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh: Omega
Ubermosh: Omega
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh: Santicide
Ubermosh: Santicide
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh Vol.3
Ubermosh Vol.3
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh Vol.5
Ubermosh Vol.5
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh Vol.7
Ubermosh Vol.7
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.
Ubermosh: Wraith
Ubermosh: Wraith
Scoring achievements that can sometimes be incredibly hard to do with underpowered classes.

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