Elder Scrolls: 10 Best Dark Brotherhood Assassinations
8. A Watery Grave
This is the first main assassination in Oblivion and it perfectly sets the precedent for the best quest-line in the game. You have to sneak aboard a pirate ship and take out the captain. A simple quest that can be completed in many different ways.
It really stresses the freedoms you have in tackling these missions. Whilst most people will simply stow away in the cargo, it is incredibly easy to break in through the balcony window and kill your target there.
It's certainly not the best quest in the guild, but it is one of the most memorable as it is the one that sets the tone for the rest of them. And it does that job perfectly.