Jimmy Wales has a question for you:
Imagine there existed a budget of $100 million to purchase copyrights to be made available under a free license. What would you like to see purchased and released under a free license?
Hmmm...I'd start with a good newspaper archive, like The New York Times. I'd make every article ever written completely accessible and free. Then, for purely selfish reasons, I'd go ahead and make Bob Dylan's entire music catalogue open access. If I had any money left over, I'd put introductory textbooks online. Shouldn't every kid have access to a lucid book on the basics of biology? Or a clear guide to macroeconomics? If I still had money left over, I'd digitize The New Yorker archives, followed by the collected works of W.H. Auden and William James.
Not sure if you don't already know, this, but The New Yorker is already digitized, atleast 80 years worth of it. Not free, but $100 doesn't seem too costly for that many issues.
http://www.thelibraryshop.org/newyorkercomp.html