On stackoverflow podcast 11:
Spolsky: Yep. There's a new product also, if you don't want to use the Team System there our friends at Redgate have a product called SQL Data Generator [http://www.red-gate.com/products/sql_data_generator/index.htm]. It's $295, and it just generates some realistic test data. And it does things like actually generate real cities in the city column that actually exist, and then when it generates those it'll get the state right, instead of getting the state wrong, or putting states into German cities and stuff like... you know, it generates pretty realistic looking data. I'm not really sure what all the features are.
This is probably not what you are looking for, but it might be a good starting off point, instead of creating your own.
I can't seem to find anything in google, so I would suggest tackling the problem by parsing a given regular expression into the smallest units of work (\w, [x-x], \d, etc) and writing some basic methods to support those regular expression phrases.
So for \w you would have a method getRandomLetter() which returns any random letter, and you would also have getRandomLetter(char startLetter, char endLetter) which gives you a random letter between the two values.