The Commanding Heights
A six hour documentary archived online chronicling the entire economic history of the world in the 20th Century. Simply the most amazing and educational experience ever.
Easily viewable in 4-8 minute chapters:
http://www.pbs.org/wgbh/commandingheights/lo/story/index.html
For a full and in-depth understanding of why Free Markets, Private Property, Individual Liberty, and the Rule of Law have proven beyond a doubt to be superior to any type of statism - socialist or totalitarian in the crucible of the real world.
Extraordinary interviews with the major individuals of the 20th century, including Friedrich Hayek, Milton Friedman, Margaret Thatcher, George Schultz, Newt Gingrich, Mikhail Gorbachev, Lech Walesa, Jorge Quiroga (the President of Bolivia), James Baker, and many, many others.