The problem often is, the data does not go back very far, or it does not reflect total return.
I discovered you can very easily get total return data for the S&P 500 in a spreadsheet for the last 63 years, since 1950. Here's how:
1. Go to http://finance.yahoo.com/
2. At the top of the page, just under the date, is some blue text: "S&P 500". Click on that.
3. On the next page, there is a menu on the left hand side. Click on "Historical Prices".
4. On the next page, you can choose a date range, and daily, weekly or monthly. Your choice. If you do change the defaults, click "Get Prices" to refresh the page. Otherwise, skip this step.
5. Note that the last column in the table is "Adj Close*". Scroll to the bottom of the page. Note that at the bottom of the table it says: "* Close price adjusted for dividends and splits". Click on "Download to Spreadsheet".
6. The result will be a downloaded csv file that you can open in Excel or any similar spreadsheet.
7. In the spreadsheet, you only want to keep the leftmost (date) column, and the rightmost column (Adj Return) which you should rename "Total Value". Delete the intervening columns.
8. Save the spreadsheet as something like "S&P 500 Total Return".
Now you have a very cool resource, and you do not need to be a total Excel or financial geek to use it. For example, if I invested $100 on January 1, 1995, what would it be worth today? The answer is $389.
Not very interesting, but if your question is, if I invested $100 a month for a child born in 1995 (who is now 18), would that pay for college, that is a very interesting question. It is easy to calculate. It gives you an estimate of the past, not a prediction of the future. But, is the number about $100, or $200, or $300, or ...?
Another interesting thing I did not have a feel for, is the following: What fraction of the time has the market been higher than today (edit: than on a given day)? After one month, after one year, ... ?
Here are the results:
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1 Mo 3 Mo 6 Mo 1 Yr 2 Yr 5 Yr 10 Yr 59.4% 64.6% 68.7% 72.7% 80.3% 80.7% 90.6%