Set your recorders! Monday Night Football will have some competition tonight from a PBS special on the Stock Market Crash of 1929. I have seen reviews for it and it looks very good.
PBS even provides teaching notes but they seem more suited for high school. One tip that I would suggest is to compare and contrast Fed actions following the crash of 1987 (and the attacks of 9-11 for that matter) and what happened after the 1929 crash.
PBS' timeline is also interesting. It shows much of the history that is inherently tied to the current marketplace. Related to this idea, I recently purchased Wall Street: a history from its beginnings to the fall of Enron of Wall Street. I am only about 25 pages in to it, but so far so good. It is always useful to see how "big" events influence history. For example, the 1929 crash led to the strengthening of the Fed and the creation of the SEC.