Elder Scrolls: 10 Best Dark Brotherhood Assassinations
3. Breaching Security
The best quest in Skyrim's Dark Brotherhood is one that leaves you completely to your own devices. You get given the name of the target and the place in which to find his schedule. The rest is completely up to you.
You can plan to intercept him on the road where he will be most vulnerable or wait patiently in the place he's going to sleep in a couple hours. You really play the role of the assassin rather than just a lackey performing the usual quests.
All that's without mention he's the son of one of the most annoying characters in the game, with his death being incredibly satisfying on that part.