Highlights

  • Ruining parties and causing chaos can be oddly satisfying, especially when it involves taking down untrustworthy figures and destroying their homes.
  • The Elder Scrolls 4: Oblivion is filled with quests that require the player to ruin things in order to succeed, and these quests provide a strange sense of enjoyment.
  • Whether it’s destroying a magic tree, ruining someone’s home, or bringing down a corrupt official, the game offers a selection of quests that allow the player to take satisfaction in spoiling others’ plans.


Trying hard to save the day is one thing, yet ruining everything and still beating a quest is quite a peculiar thing in itself. After all, there’s a strange satisfaction that comes with spoiling parties, becoming a thorn in the side of untrustworthy figures, and trashing a person’s home for the joy of a pair of untrustworthy workers.

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Whatever the intentions are, be they honorable or mischievous (or, just wanting some kind of reward by the end of it), The Elder Scrolls 4: Oblivion is filled with quests that have a player ruining things to succeed, and these are a selection of the best ones.


1 The Hist

Destroying The Blackwood Company

10 Things About The Hist Tree Sap

  • This is a quest from the Fighters Guild story.
  • After infiltrating a rival paid-for-hire company’s ranks, it is revealed that they have consumed a drug from a magic tree inside its halls.
  • The side effects result in innocent lives being taken unknowingly by the mercenaries. Ergo, the tree and anyone guarding it must be destroyed.

The Fighters Guild begins to feel the tension in competition from the seemingly perfect Blackwood Company. After infiltrating its ranks, it’s revealed that they consume Hist, a drug produced by a magic tree that makes its users go into a fighting frenzy. During the first mission, the hero unknowingly joins in with killing a town of civilians.

Thus, the Hist tree must be destroyed. Returning to Blackwood Company, the player’s cover is blown, and everyone will become hostile. Even the former Fighters Guild weasel Maglir will pop out, saying how his life and career are ruined, before attacking. Bringing the Blackwood Company organization to its knees is clearly the right thing to do, and a satisfying one at that.

2 Everything In Its Place

Ruining Cindanwe’s Life

Elder Scrolls IV Oblivion Shivering Isles - Two farmers chatting near the water and a bridge

  • In the Shivering Isles, southeast of The Fringe is a farming village called Fellmoor.
  • The untrustworthy Khajiit workers are insistent that their overseer, Cindanwe, is reading their minds and controlling what they think.
  • Murdering Cindanwe, or trashing her home, will appease the workers.

Fellmoor is home to a pair of Khajiits, the lying Ranaar-Jo and the paranoid Kishashi. The latter will ask the player to remove their overseer, an Altmer named Cindanwe, and optionally loot her diary. Killing her is one option, but causing a mess in her home by knocking things over will also work.

This is an interesting quest. Not only are both of the quest-givers deluded (as is expected in the Realm of Madness), but it’s clear that Cindanwe is actually struggling to keep her thoughts intact and needs everything neat and orderly. She’ll be left in despair if her home is ruined. Honestly, one can’t help but feel bad for whatever tactic is chosen here…

3 Imperial Corruption

Putting Away A Corrupt Watch Captain

Elder Scrolls IV Oblivion - Imperial City Citizens standing around in daytime

  • Rumors in the Imperial City will reveal Ruslan and Luronk gro-Glurzog were fined by a corrupt Imperial Watch captain.
  • The player can bring the corrupt official’s career to a grinding halt by alerting another captain and persuading the victims to testify.
  • After justice is served, the crooked guard will escape prison and hunt the player down.

Ruining an Imperial Watch captain’s career sounds cruel, though this particular figure deserves it. Close friends Ruslan and Luronk gro-Glurzog reveal Captain Audens Avidius fined them at a local shop after false accusations of thievery. After questioning the shop owner, the player can alert another captain, Itius Hayn, who will need two additional spectators to come to him to testify.

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If successful in doing so, Avidius is arrested and jailed. Ten days later, he’ll escape prison and stalk the hero wherever they are, attacking them with an iron dagger. Considering how, if accused directly in conversation with him, he’ll even falsely accuse the player of assault and charge them with a 1,000 gold fine, both ruining his career and finally cutting him down is only a befitting end to such a rotten figure.

4 Corruption And Conscience

Sending A Crooked Guard To Prison

Elder Scrolls IV Oblivion - Ulrich Leland threatening the player

  • Rumors in Cheydinhal mention steep fines imposed by a guard captain.
  • One civilian has lost his home and stumbles drunkenly on the streets. Eventually, he’ll be killed for fighting a guard.
  • The player can end the crooked guard’s career in three satisfying ways.

Captain Ulrich Leland of the Cheydinhal guard is yet another corrupt figure who has been imposing ridiculous fines. After speaking to one of his evicted victims, Aldos Othran, he’ll foolishly fight the sentry guarding his former house, only to be cut down.

From here, the quest splits into three different paths: kill Leland, lure him to a friend of Othran’s to exact her revenge on him, or uncover his schemes. Turns out, in the third option, he’s using the collected money to pay for gifts! Getting him sent to jail is a gratifying solution, not only because one can reap the most rewards alongside a Fame bump, but also because it completely spoils his devious plans while he rots in jail for the rest of the game!

5 Taking Care Of Lex

Ruining Lex’s Career

Elder Scrolls IV Oblivion - A desk ready to be plundered and looted

  • This is a quest from the Thieves Guild storyline.
  • The pompous Hieronymus Lex must be removed as a threat to the Thieves Guild.
  • The most humiliating way to do so is to have him be reassigned as a captain of the Anvil City Watch, leaving him unable to hunt for the organization’s leader anymore.

Hieronymus Lex has been humiliated by the Thieves Guild numerous times in their storyline, thanks to the player. In “Taking Care of Lex,” his hunt for the guild and its owner, the Gray Fox, can be stopped permanently. Since murder is strictly forbidden, one must steal a recommendation letter from Anvil, bring it to a forger, get a fake version sealed by the Imperial Legion Offices, and deliver it to Anvil’s ruler, Countess Umbranox. This would force him to work in Anvil.

After delivering the news to Lex, the pompous captain is powerless. Being the vital component in his transfer, after all that sneaking through heavily guarded castle depths, is delicious. After all the previous missions, the player gets to spoil Lex’s hunt for the guild, and his lifelong goal finally crumbles.

6 Through The Fringe Of Madness

Rendering The Shivering Isles Defenseless

The Gatekeeper

  • After entering A Strange Door to Passwall, a seemingly invincible Gatekeeper is found protecting the entrances to the rest of the Shivering Isles.
  • He serves as a bodyguard and decimates a group of bold adventurers attempting to fight their way through.
  • A few solutions are on offer to remove the realm’s guardian and enter either Mania or Dementia.

Entering Sheogorath’s realm and killing his Gatekeeper is one heck of a way to make a first impression with the Madgod. Naturally, this causes some complications in the main story, though it’s a great quest nonetheless. This hardy, tough creature is tasked with preventing “tourists” from wandering into the rest of the realm and thus must be removed to progress.

Its creator, Relmyna Verenim, visits her creation every night, and cries in his presence; those tears can be used as an ability-nullifying poison. The local bone-obsessed Jayred Ice-Veins wants him dead and will team up with the protagonist with special bone arrows to deliver serious damage. Of course, a powerful weapon can cut him down with enough effort. Either way, the realm will be missing one Gatekeeper, to its inconvenience.

7 Baiting The Trap

Driving Three Adventurers Insane

Elder Scrolls IV Oblivion Shivering Isles - A room full of zombies, an adventurer is turned into a ghost

  • In the Shivering Isles, the player is directed to Xedilian to activate the Resonator of Judgement.
  • This is intended to direct intruders into the realm to their doom.
  • In this quest, two options are offered in three different scenarios; whether the adventurers can be killed or driven to madness.

With the Shivering Isles missing a Gatekeeper, and after attuning the Resonator of Judgement in a previous quest, its true purpose comes into play: doom three adventurers. It’s a simple enough quest, though a deliciously devilish one where one can choose between death, or destroying the victim’s sanity.

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For example: a cage surrounding a pile of gold is on display. Both a Dark Elf and an Orc attempt to see if they can break through. The red button launches fireballs that kill the Dunmer. Alternatively, the green button will unleash a ton of fake keys that will drive the elf insane as he frantically tries to find one that’ll fit the lock. Whatever choices are made, the player can take pride in knowing they brought their adventures to a startling halt in the nastiest ways possible.

8 Sanguine

Crashing A Party

Elder Scrolls IV Oblivion - Shrine of Sanguine and his followers at night

  • Players will come across a statue of Sanguine west of Skingrad.
  • The player must cast a spell on a group of party-goers in Castle Leyawiin.
  • The party will be ruined if everyone’s clothes are stripped off by the spell.

The Daedric lord Sanguine has some choice words about the Countess of Leyawiin and her party. So, the player is tasked with infiltrating the celebrations and casting “Stark Reality” upon everyone present. Everyone afflicted is stripped of their clothing and possessions, the protagonist included, and will turn hostile.

Finding a way into a restricted party without an invitation, only to cause chaos inside for everyone, is a joy to take part in. Running away, breaking out of prison, or trying to use Charm spells are all viable and entertaining solutions to get back all the goods that Sanguine has stashed away conveniently.

9 Whodunit

Turning Partygoers Against Each Other

whodunit quest in Oblivion

  • This is a quest from the Dark Brotherhood storyline.
  • A group of people are invited to a party inside Summitmist Manor. Each must be killed, preferably without one another knowing, for a bonus reward.
  • Various solutions on offer make this a fan-favorite quest.

Speaking of crashing parties, “Whodunit” is a fan-favorite for its sheer variety of how to kill everyone present in a gathering at Summitmist Manor. The targets are fooled by the guise of a treasure hunt when they’ve been unknowingly lured to their doom.

Simply slashing everyone one by one spoils the fun and forfeits the bonus reward. The best way to approach it is to be creative. Each guest has varying responses to give to the player and one another, and with a silver tongue, they can be manipulated into killing one another, luring themselves into separate spaces, and so on. Watching everyone break down from the paranoia and suspicion heightens the tension and makes the whole thing feel sadistically sweet.

10 Purification

A Family Destroyed

Elder Scrolls IV Oblivion - approaching Ocheeva with the Blade of Woe

  • This is a quest from the Dark Brotherhood storyline.
  • Everyone in the Dark Brotherhood of the Cheydinhal Sanctuary must be killed to root out a potential traitor.
  • To be supported by such a memorable cast of killers, only to have to kill them all, is a painful task for fans.

Everything seems to go smoothly for the protagonist in the Dark Brotherhood storyline before being told to visit Fort Farragut. There, Lucien Lachance, the man who first recruited the player into the guild, reveals that a traitor is present and that everyone in the Cheydinhal Sanctuary must die.

Considering how likable everyone there was, it’s so difficult to put them all to death. Naturally, poisons, sneak attacks, spells, and the like will dispatch them without much fuss, but they’ve treated the player like a family for all this time. Even the sour, bitter Khajiit mage M’raaj-Dar suddenly has a change of heart and treats the protagonist much better at the most bitterly ironic time. It really does feel like all of this love and stability has to be torn asunder, but, the rules are the rules: a Purification requires no survivors.

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