According to data from Shiller we have never had an S&P 500 with negative earnings. Of course his data only go back to 1871.
Estimates are now out for negative earnings on the S&P 500. So I guess we stop talking PE or yield and start looking around at the e-bay resale value of firms assets less loss rate.
Every era creates it own novel corporate valuation metric. The new metric for company valuation is probably the PY ratio which is the Price to Yard sale ratio of a firms assets.
Please note the yard sale below is supported by a handy TARP. I knew that thing had some uses.