Profanity filter import

Question 1

As the Tin Man suggested, this problem is difficult, but it isn't impossible. I've built a commercial profanity filter named CleanSpeak that handles everything mentioned above (leet speak, phonetics, language rules, whitelisting, etc). CleanSpeak is capable of filtering 20,000 messages per second on a low end server, so it is possible to build something that works well and performs well. I will mention that CleanSpeak is the result of about 3 years of on-going development though.

There are a few things I tell everyone that is looking to try and tackle a language filter.

Don't use regular expressions unless you have a small list and don't mind a lot of things getting through. Regular expressions are relatively slow overall and hard to manage.
Determine if you want to handle conjugations, inflections and other language rules. These often add a considerable amount of time to the project.
Decide what type of performance you need and whether or not you can make multiple passes on the String. The more passes you make the slow your filter will be.
Understand the scunthrope and clbuttic problems and determine how you will handle these. This usually requires some form of language intelligence and whitelisting.
Realize that whitespace has a different meaning now. You can't use it as a word delimiter any more (b e c a u s e of this)
Be careful with your handling of punctuation because it can be used to get around the filter (l.i.k.e th---is)
Understand how people use ascii art and unicode to replace characters (/ = v - those are slashes). There are a lot of unicode characters that look like English characters and you will want to handle those appropriately.
Understand that people make up new profanity all the time by smashing words together (likethis) and figure out if you want to handle that.

You can search around StackOverflow for my comments on other threads as I might have more information on those threads that I've forgotten here.

Question 2

Here's one you could use: Offensive/Profane Word List from CMU site

Question 3

Based on personal experience, you do understand that it's an exercise in futility?

If someone wants to inject profanity, there's a slew of words that are innocent in one context, and profane in another so you'll have to write a context parser to avoid black-listing clean words. A quick glance at CMU's list shows words I'd never consider rude/crude/socially unacceptable. You'll see there are many words that could be proper names or nouns, countries, terms of endearment, etc. And, there are myriads of ways to throw your algorithm off using L33T speak and such. Search Wikipedia and the internets and you can build tables of variations of letters.

Look at CMU's list and imagine how long the list would be if, in addition to the correct letter, every a could also be 4, o could be 0 or p, e could be 3, s could be 5. And, that's a very, very, short example.

I was asked to do a similar task and wrote code to generate L33T variations of the words, and generated a hit-list of words based on several profanity/offensive lists available on the internet. After running the generator, and being a little over 1/4 of the way through the file, I had over one million entries in my DB. I pulled the plug on the project at that point, because the time spent searching, even using Perl's Regex::Assemble, was going to be ridiculous, especially since it'd still be so easy to fool.

I recommend you have a long talk with whoever requested that, and ask if they understand the programming issues involved, and low-likelihood of accuracy and success, especially over the long-term, or the possible customer backlash when they realize you're censoring them.

Question 4

I have one that I've added to (obfuscated a bit) but here it is: https://github.com/rdp/sensible-cinema/blob/master/lib/subtitle_profanity_finder.rb