I got out of college in 1980 and went to work for Arthur Andersen in Houston doing E&P and drilling company audits and IPOs and around that time oil peaked at about $40/BBL. In 1980 the dow jones industrial average was just under 1,000.
Although $300 seems very high, using the relationship of WTI to the DJIA in 1980, applied to the current price of the DJIA, today's oil price would be about $1,350/BBL ($40/$1,000 x $33,500).
Granted, the DJIA was probably undervalued in 1980 and overvalued today but even so oil appears real cheap today relative to the stock market. Markets always seem to overextend (up and down) and $300 oil would seem to be an overextension but don't assume it's not possible.