The last time the S&P 500's Shiller cyclically adjusted P/E ratio was as high as it is now, it was August 2000. The S&P 500 was sitting near an all-time high of around 1,500, in the wake of a five-plus-year bull market. At the time, the Shiller ratio -- which gauges the 10-year inflation-adjusted valuation of the S&P 500 -- was at 41.89, down from an all-time peak of 44.19 in November 1999. What was unclear at that point was that the market was already at the beginning of a bear market that would last until November 2022. Image source: Getty Images.
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