In my Wills and Estates class the other day I learned of a website called Measuring Worth.com. This site lets you measure the historical worth of a dollar. A dollar from my birth year is worth from $5.01 to $16.63 today depending on what measure you use. Using the Consumer Price Index which is the most common measure you get a value of $6.21. That helps you realize the effect of inflation.
They also have several other calculators including one that lets you measure what a historical investment in the Dow Jones, S&P 500, or Nasdaq would have returned. Those returns don’t include reinvested dividends though which makes the returns lower than they should be. Also, for those from the United Kingdom they have calculators for the pound using the UK GDP, CPI, and other data.