10 Most Surprising & Creative Side-Quests In Video Games

In video games, we’re always hungry for something more. Something off the beaten path. We like to explore every nook and cranny of a game, because we’re naturally curious — a developer made all this, so there has to be a reason for it. And finding something special like a totally unique or weird side-quest is often our reward. Side-quests are a fine art in video games. A good side-quest surprises us and deepens our love for a game. A bad side-quest is boring drudgery that nobody wants to do. Today, we’re going to talk about some of the most fun, weird, wacky and wild side-quests we’ve ever come across. These are the most creative quests, the ones that put a spin on the normal formula, that do something a little unexpected that we’ll never forget.

We’re still talking about some of these old side-quests. Some side-quests have stuck with us for 20+ years, and there are plenty more we’d love to talk about here. Its impossible to list every awesome side-quest in video games, so these are just the ones that took us by surprise. That jumped out and did the unexpected. These quests shattered our expectations for what a side-quest can and should be. Sometimes they’re the best parts of their respective games! We’ve got to salute the incredibly creative developers that put in the extra effort to give us something fun, clever, and creative to discover.


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Whodunit [Elder Scrolls 4: Oblivion]

One of the most creative side-quests in any RPG, and what was for many of us the most memorable moment of Oblivion. Whodunit really is that good. Guests are trapped inside a hotel, and they’re dropping like flies. You’re tasked with discovering the murderer before morning, and you’ll have to talk to each character to get clues and pick your suspect. And here’s the big twist — you’re the killer.

This is a Dark Brotherhood quest, and the guests are your assassination targets. Instead of investigating, you’re actually picking off each guest secretly. In conversation, you can turn the guests against each other. You’ll have to take them out one-by-one stealthily so you’re not caught, all while keeping up the ruse that you’re a benevolent detective. It’s a dark, twisted little side-quest that’s also one of the most creative in the entire game.


Ribbons [Silent Hill: Downpour]

No one’s going to say Silent Hill: Downpour is the best Silent Hill game, but it does have one strong thing going for it. The side-quests are surprisingly involved and creative, and Ribbons is one of the best. After finding a flyer for a missing girl, you’ll quickly encounter clues — her mother leaves ribbons hanging around town to tell her where to go. Following the ribbons leads you all around the abandoned town of Silent Hill. And this quest gets dark.

The ribbons lead all the way to a pier. The little girl’s mother has trained her well — she absolutely must follow the rules. Red ribbons for left, yellow ribbons for right. The last ribbon you’ll find is right at the bend on the dock with a scrap of clothing left behind and a key to the mother’s apartment. Find your way back to their home, and you’ll find a note all about the mother’s quest to get rid of her child. Its a memorably twisted, horrific ending to a clever little side-quest.


Sunry’s Trial [Knights of the Old Republic]

Who expected a courtroom drama in KotoR? On the planet Manaan, your party can get embroiled in a murder trial — as an impartial Jedi, you’re the best pick to defend a man accused for murder, right? Like a good Ace Attorney case, you’re immediately sent out to investigate the crime scene and determine whether Sunry is guilty or innocent. Your job as Legal Defense is to do your best, but is that possible when you know that Sunry is guilty?

The case isn’t ambiguous — if you do enough digging, you can find definitive proof that Sunry is a murderer and is part of a Sith plot. You can choose to keep his secret and find him Not Guilty, or you can reveal his crimes and fail as a Defense Attorney. What’s the right choice in all this?!


The Harvester [Deus Ex: Mankind Divided]

The longest-running and best side-quest in Mankind Divided is absolutely The Harvester. Eventually as you’re exploring your new city, you’ll encounter a washed-up detective trying to find the identity of a serial killer. You’ll have to talk to suspects and try to figure out who the real killer is — a fun premise for any action-RPG! We’ve got a lot of detective side-quests here, and they’re always awesome just for the depth of their story-telling and the puzzling gameplay. These are side-quests, so you can fail if you make the wrong choice.

The big twist is that none of the suspects are guilty. Instead, you’ll later encounter the witness to the crime. She lives in the same building as our hero Jensen, and if you break into her apartment, you’ll find she’s been spying on you. The witness purchased an illegal cybernetic enhancement from a deceased serial killer, and his mind is overwriting the witness’s — if you don’t figure her out, she can lead you into a trap that’s more difficult to escape than any of the normal boss fights in the game. Just an extremely fun and surprising series of side-quests.


Job Interview [Hitman 2]

Hitman 2 can be wickedly funny, and the Job Interview side-quest is one of my favorites in the entire series. The rebooted Hitman series of games drop your assassin into a toybox world of moving parts, and you can get involved in a multitude of secret ways. In the New York Bank mission, Agent 47 can take the place of a prospective new employee, going into the job interview and selecting answers to different questions. Depending on your answers, Agent 47 can get a variety of different jobs.

If you answer like a true predator — something a master assassin like Agent 47 can do with darkly humorous irony — you’ll get a job at the Executive Level, giving you instant access to the top floor where your target is waiting. If you answer wrong, you’ll get progressively worse jobs. Its a hilarious little skewering of corporate culture and shark-in-the-water stockbrokers. Agent 47 looks positively sane in comparison.


The Runaway Son [Nier]

One of the most infamous quests from Nier, a game that’s all about infamous quests. Unlike the other side-quests on this list, this isn’t really fun — in fact, this quest is annoying, slow, and completely obnoxious to complete without a guide. Not that it’s even that hard. It isn’t! The entire thing is a cruel slap in the face to the player. That’s kind of Nier’s MO.

A father asks you to find his lost son. Each time you find him somewhere in the open-world, he’ll run away. You need to keep tracking him down, hoping against hope you can find whatever new random location he’s in. If you find him enough, you’ll send him back to his father. That’s when you learn the boy’s father is a con artist and a criminal. The boy wants nothing to do with him, but you send him back to the father anyway. And for all your hard work? You’ll earn exactly no reward! The con artist just conned another mark.


Anju’s Anguish [Legend of Zelda: Majora’s Mask]

The longest and most complex side-quest in Legend of Zelda: Majora’s Mask requests you to fully engage with the game’s time-travel mechanics. In Majora’s Mask, you have three days until the town of Terminus is destroyed by the falling moon. In those three days, characters and events will transpire in real-time. In this tightly-scripted quest, you need to do everything you can to reunite two lovers. There are multiple masks and rewards along the way, making this one of the best quests to complete — and its all 100% optional.

To really get into why this quest is special, you need to play it for yourself and work on discovering each step alone. Following a guide doesn’t do this side-quest justice at all. The fun is all in discovered each step through exploration and patience. For example, to meet up with one character, you have to wait until the mailman arrives at their door. For a brief time in the 3-day window, you can dart inside the open door and finally talk to them.

By the end, you’ll hope for a happy ending for this couple as they ride out the apocalypse together. By the end, Anju and Kafei are longing for each other, but you need to complete each step to bring them home. You’ll even have to enter a dungeon and complete puzzles while playing as Kafei. There’s a reason people are still talking about this quest 20+ years later.


Checking Up With Paz [Metal Gear Solid 5: The Phantom Pain]

Some games don’t label their side-quests. Metal Gear Solid 5 is just that type of game — it is packed with weird details, mysteries, and (some) half-finished content. Thankfully, this is one bizarre series of “side-quests” that absolutely does have a resolution. Before The Phantom Pain, there was the bite-sized Ground Zeroes, where legendary soldier Big Boss must sneak into an American military camp to retrieve a kidnapped (sorta) ally. Paz is a complicated character to get into, but she has a complicated history with Big Boss. Naturally, Big Boss and his army want to recover her for their own purposes.

Until everything goes south. After rescuing Paz and extracting, Big Boss returns to his base in chaos. Enemy soldiers are everywhere, and eventually Big Boss and Paz are shot down. Much later in the game, its revealed that Paz has somehow survived her plane crash, appearing in a medical bay in your new base of operations. You can visit her between missions — which is completely unmarked, so you’ll have to fully explore your base to even find her, and you’ll have to do it multiple times.

It all ends with a revelation we all should’ve seen coming. Paz was dead all along, but her spirit remains. Paz means “peace” after all, and peace is dead. There was no hope for a happy ending when it comes to Big Boss and his crew.


The Mystery of Cainhurst Castle [Bloodborne]

Bloodborne is yet another game that doesn’t track side-quests. None of the Soulsborne games developed by From Software have side-quest markers, but they absolutely do have side-quests. And Cainhurst Castle is absolutely the most incredible side-quest in the developer’s history so far. Cainhurst is a spooky castle that’s creepy even by the cosmic horror vibes of the original. The castle is frozen in time, and populated by bloated, blood-drunk women-mosquito hybrids. Inside is even spookier, as ghosts roam the hallways of the great library. Gargoyles spring to life on the outer walls, and servants avoid you completely as they continue to clean the blighted floors of this old castle.

Cainhurst is an important part of the lore, and ends with a terrific boss battle. It is such a cool location, it feels silly calling this a side-quest. In many ways, this is one of the best parts of one of the best games of the PS4 generation. Of course everyone needs to see it! If a side-quest feels mandatory just because it’s that great, it absolutely belong here.


Self-Reflection [Control]

Control is packed with clever, weird, and twisted side-quests that come out of nowhere. Sometimes you’ll do your best to rescue lost FBC agents, and sometimes you’ll enter planar realms ruled by cyclopean eyeball monsters. For my money, my favorite is Self-Reflection. In this weird quest, you have to travel deep into a lab studying the strange effects of synchronization — if you haven’t played Control, its hard to explain all this stuff. Cutting to the chase, there’s a weird mirror that leads to an alternate reality.

Entering the mirror flips everything. The map is now flipped, and even the dialogue people speak is backwards. This alternate reality isn’t just inverted. Everything is opposite, and as you return to the large room, you’ll encounter a twisted flipped version of yourself called esseJ. Whatever you encounter in the mirror is directly opposed, and our hero Jesse is known for shooting anything that doesn’t belong in our reality. No surprise that Mirror Jesse is exactly the same. Just flipped.


That’s just a fraction of some of our favorite side-quests of all time! Let us know about your favorite (or least favorite) side-quests!