Shakespeare is particularly evil in this regard, given the terms he coined. Some we have picked up and others haven't made it to the modern age.

But, extra credit for compressing such that it still pentas its iambic meter. :-)

It would be fun to take arbitrary slices of force-ranked words and constrain composition likewise. Words of ordinal frequency 1500-3000 would create a bit of a challenge along the line of writing a book without a single letter e. (http://books.google.com/books/about/Gadsby.html?id=jG1JU82Bd...)