Shady Sam in Oblivion (including Oblivion Remastered) is found outside the walls of the Imperial City, specifically in the northwestern part near the Elven Garden District. To locate him, fast travel to the Chestnut Handy Stables and then head northeast along the city wall. He typically stands beside the wall on the right as you move from the stables towards the Elven Garden District. He is dressed in black with a hood and is known to sell lockpicks, skooma, and various poisons. Shady Sam is available day or night but will flee if guards approach, and he doesn't engage in the persuasion mini-game for haggling prices. To summarize:
- Location: Outside the Imperial City walls, near the Chestnut Handy Stables, northwest part near Elven Garden District.
- How to find: Fast travel to Chestnut Handy Stables, head northeast along the wall until spotting him.
- Inventory: Lockpicks (in bulk), Skooma, poisons, potions.
- Behavior: Available day/night; flees if guards come close; no disposition increases or haggling mini-game.
This makes Shady Sam a reliable early-game vendor for lockpicks and illicit items.