Like the $1,000 bill these were last issued in 1934. One of these would buy a brand new car at the time.

 

$500 1934A Federal Reserve Note New York FR2202B PMG 25 VF

Series of 1934-A $500 bill, FR2202B BA Block Julian Morgenthau, S/N B00385529A pp E, Federal Reserve Note New York. This $500 bill is graded a 25 Very Fine by PMG.