If you’re jumping into The Elder Scrolls IV: Oblivion Remastered, chances are you’re ready for some classic dungeon crawling, Daedric deals, and NPCs with those unforgettable, awkward stares. But in between the usual quests are some truly bizarre side missions. These still hold up as some of the weirdest content Bethesda’s ever put in a game. Whether you’ve played them before or you’re brand new, these side quests will make you laugh, scratch your head, or wonder about Bethesda. It’s like someone there was sleep-deprived and having a little too much fun.
Whodunit?

This is many people’s favourite quest due to how bizarre it is. It’s a murder mystery where you’re the killer. You’re thrown into a creepy manor with five guests. You’re told to take them out one by one without being caught. It’s like playing Clue, except you’re the guy with the knife!
A Brush With Death
You’re tasked with finding a missing painter, which seems like standard stuff. You might think nothing is unusual. However, nothing is standard after you pick up a magical brush. You then get sucked into a magical painting. You have to fight off trolls using enchanted turpentine. That’s right, turpentine. It’s creative and artsy (literally). Plus, it’s completely unhinged.
Paranoia
As is referenced in the quest title, a paranoid Wood Elf in Skingrad begs you to spy on his neighbors. He’s convinced they’re out to get him. I won’t spoil things in case you’ve never done this side quest. It starts off funny before (typically) getting dark real fast, depending on how you handle it. This is par for the course for most Bethesda titles.
Through A Nightmare, Darkly
Remember the movie Inception? Well, it’s like that. You enter a guy’s dreams to rescue him from a magical coma. It plays out like a dream-world version of therapy. This is complete with twisted versions of his past and childlike versions of himself. Super trippy.
The Hist Dream
This could arguably be considered not a side quest as it is part of the main Fighter’s Guild quest line. However, since joining those is (as with many things in the game) completely optional, I chose to include it. You end up hallucinating after drinking tree sap. You then fight your way through a jungle dream sequence. It’s like Oblivion suddenly took a turn into experimental art.
Shrine of Namira
Basically you help a bunch of depressed outcasts by making them feel worse so they can gain dark powers. It’s uncomfortable, weird, and very on-brand for an Elder Scrolls game.
Conclusion
Oblivion Remastered might come with prettier graphics and better performance, but the real charm is still in its totally bonkers side quests. These aren’t just filler; they’re the stuff that made Oblivion legendary. If you’re only sticking to the main questline, you’re missing out on some of the strangest moments. You would also miss some of the most creative moments in the whole game.
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