Optional Missions That Went Way Too Hard
Side quests are supposed to be the fun little extras you chase between main story beats. They’re great places to meet someone new or discover a hidden treasure somewhere you wouldn’t have explored otherwise. At least, that’s the case in a perfect world. In reality, some games use them to drop their bleakest material when your guard is down. Here are 20 side quests that revealed the darkest parts of a game and made players realize the optional path wasn’t exactly light entertainment.
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1. “The Bloody Baron’s Family Matters” - The Witcher 3: Wild Hunt
The Bloody Baron’s questline starts like another grim errand, but it quickly turns into one of the game’s most uncomfortable looks at domestic abuse. As Geralt investigates what happened to the Baron’s wife and daughter, the story just makes you feel worse and worse, and by the end, the monster contract is almost secondary to the damage people can do inside their own homes.
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2. “No Stone Unturned” - Red Dead Redemption 2
Oh, what do you know? Another day, another side quest where Rockstar scares us. Forget a gentle horse ride through the Heartlands; it doesn’t take long for you to find one of three mutilated bodies arranged like messages. Somehow, it only gets worse the more you dig.
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3. “The Dunwich Building” - Fallout 3
The Dunwich Building looks like another ruined office full of ghouls, doesn’t it? Yeah, that’s only until the audio logs and visions kick in. Instead of a simple scavenging run, you uncover a slow descent into madness tied to cult activity and something that feels older than the wasteland itself. That’ll teach you to look off the beaten path.
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4. “The House of Horrors” - The Elder Scrolls V: Skyrim
A random investigation in Markarth turns into a Daedric nightmare when Molag Bal drags you into his little game. The quest forces you to participate in cruelty, and even if you do it “successfully,” you’ll still feel like a loser. No one wants to participate in a bargain they’re pushed to accept.
5. “Sinnerman” - Cyberpunk 2077
For a game loaded with bugs, they sure knew how to hide some of the freakiest treasures in its side quests. “Sinnerman” begins as a revenge job and spirals into a deeply uneasy story about faith, media exploitation, and public execution. Joshua Stephenson’s desire to turn his death into a spectacle is disturbing enough, but the people eager to profit from it make Night City even colder.
6. “The Man Who Killed Jason Foreman” - Fallout: New Vegas
This unmarked story around Westside and the Fiends shows how much damage one violent guy can leave behind. When you learn what happened to Jason Foreman and how his death affected the community, the wasteland’s chaos gets dragged to a very personal level.
7. “The Riddler’s Hostages” - Batman: Arkham City
Well, “The Riddler” and “hostages” are rarely two things you want to see in the same sentence. They’re not something you want to see in a side mission either, but if you poke around, you’ll unlock puzzle-box busywork until you start rescuing the hostages trapped in Gotham. His obsession with proving he’s smarter than Batman really knows no bounds, and once again, it’s your problem to deal with.
8. “The Carnal Sins” - The Witcher 3: Wild Hunt
“Carnal Sins” starts as an everyday investigation in Novigrad…and slowly exposes a killer using moral panic as cover for sadism. The quest pulls you through all sorts of nightmares, like morgues and religious hypocrisy, without letting the city feel like a safe place for anyone. What makes it so nasty is the cruelty.
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9. “Vault 11” - Fallout: New Vegas
Look, it’s not our fault that we wander around Fallout! Though we wish we knew how to quit our nosy nature, especially after Vault 11. It isn’t even a traditional side quest with a big quest marker; it’s tucked away as one of the bleakest stories in the series, though. Spoiler alert, but recordings and environmental details reveal how the vault’s residents were manipulated into sacrificing one person every year.
10. “An End to All Things” - Dragon Age: Inquisition
The Chateau d’Onterre side area looks like your run-of-the-mill haunted-house detour, but it's way worse than that. Its notes and layout reveal a family tragedy built around pride and corruption, and as you piece together what happened to the Otranto family, the mansion becomes less of a spooky attraction and more of a crime scene.
11. “The Last Voyage of the U.S.S. Constitution” - Fallout 4
At first, this quest seems like one of those fun, bonkers missions you can knock out in between the main plot. But that’s how it gets you. Under the comedy, there’s a sad little picture of machines clinging to patriotic fantasies in a world that was already destroyed by those same obsessions.
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12. “The Truth” - Grand Theft Auto V
You’d think this would be more of a Trevor thing, but alas. If you’re really looking for “enlightenment,” Michael’s Epsilon Program side missions begin as a parody of celebrity cult nonsense, but the deeper you go, the more predatory the whole operation becomes. You’re asked to perform humiliating tasks, hand over money, and buy into an ugly system.
13. “Beyond the Beef” - Fallout: New Vegas
Don’t let its seemingly humorous name fool you. “Beyond the Beef” sends you into the Ultra-Luxe casino for what sounds like a missing-person case, then casually reveals the very special appetite of elites. We won’t lie, though; New Vegas is at its sharpest here, showing that the big whigs are just as savage as raiders.
14. “Return to Crookback Bog” - The Witcher 3: Wild Hunt
This follow-up to the Baron storyline gives you a chance to see the consequences of earlier choices—for better or worse. Depending on what happened, you may find a family completely shattered, leaving nothing more than grief and guilt in its wake. (Don’t you hate it when in-game events actually have consequences?)
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15. “That Lucky Old Sun” - Fallout: New Vegas
Yes, we’re back on Fallout, but don’t worry! This is our last one. How could we not mention this quest about fixing a solar power plant? Oh, sure, it sounds simple until you learn how HELIOS One can be used and who wants control of it. Then you’re smack-dab in a learning experience about whether old-world weapons should ever be allowed back into play.
16. “The Last of the Medicine” - Horizon Zero Dawn
Several of Horizon Zero Dawn’s smaller quests reveal how fear can make vulnerable people suffer. The thing is, in quests involving sick villagers and scarce medicine, Aloy often finds that the real obstacle isn’t just machines—it’s those using power to delay help.
17. “The Forgotten” - Assassin’s Creed Odyssey
No gamer wants to stumble into a quest with abandoned children and broken families, but Assassin’s Creed Odyssey doesn’t care. One of the darker threads comes from helping people who’ve been discarded by armies or relatives who no longer see them as useful. Good luck enjoying those bright islands after that.
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18. “The Missing Brother” - Kingdom Come: Deliverance
Kingdom Come: Deliverance likes to keep its darkness grounded, and it’s often only through smaller investigations that you see how fragile life is. A simple search can lead to bandits, disease, poverty, or someone nobody had the power to protect. The game doesn’t need supernatural horror to freak you out—medieval desperation does the job just fine.
19. “The Artist’s Way” - Disco Elysium
Disco Elysium does a masterful job of turning optional conversations into bleak discussions of addiction, political failure, and emotional collapse. Helping the ravers with the church or digging into the doomed commercial area can be funny for a second, but it quickly becomes staring at people who can’t get ahead.
20. “The Fool on the Hill” - Cyberpunk 2077
Collecting tarot graffiti around Night City sounds like a quiet bit of map-cleanup—emphasis on “sounds like”! In reality, it becomes a strange reflection of V’s identity crisis and approaching death. By the time the quest wraps, collectibles aren’t really rewards; they’re more like warning signs.
