Summary
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.
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: Oblivionis filled with quests that have a player ruining things to succeed, and these are aselection of the best ones.

1The Hist
Destroying The Blackwood Company
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, andeveryone 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.

2Everything In Its Place
Ruining Cindanwe’s Life
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…

3Imperial Corruption
Putting Away A Corrupt Watch Captain
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.
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 isonly a befitting end to such a rotten figure.

4Corruption And Conscience
Sending A Crooked Guard To Prison
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!

5Taking Care Of Lex
Ruining Lex’s Career
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, afterall 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.

6Through The Fringe Of Madness
Rendering The Shivering Isles Defenseless
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.

7Baiting The Trap
Driving Three Adventurers Insane
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.
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 unleasha ton of fake keys that will drive the elf insaneas 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.

8Sanguine
Crashing A Party
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.

9Whodunit
Turning Partygoers Against Each Other
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.

10Purification
A Family Destroyed
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.