This was one of the most difficult achievements for me to get in The Elder Scrolls V: Skyrim. Mostly because I was never able to do something horrible enough to warrant a 1000 gold bounty. However, pms00 has a great video tutorial showing the easiest way to get the 'Master Criminal' achievement, which requires you to hold a bounty of at least 1000 gold in all nine cities in Skyrim.
Though to pull it off like in the video, you'll need to be a werewolf in-game. All you have to do is travel from town to town transforming into your werewolf form in front of guards or citizens. Of course, there are many ways to pull this achievement off. But from everything I've gathered, this seems to be the easiest way of doing it. Just realize that if you manage to do this, you'll have a total bounty of 9000 gold. Have fun dealing with that.
- Xbox 360: 20G
- PlayStation 3: Bronze trophy
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