Large size legal tender five hundred dollar notes were only issued during the second half of the 19th century. As you might imagine, they are extremely rare to find today. If you are fortunate enough to own one of these, please let me know. I would be a buyer. Sales@AntiqueMoney.com
A very old looking James Madison is featured at the center of the 1862 and 1863 five hundred dollar bill pictured above.
Most series of 1869 bills have a similar design to the same denomination from the 1870s. However, the 1869 $500 bill is completely unique looking. There are less than five of these known to exist.
Large size five hundred dollar bills from 1874, 1875, 1878 and 1880 are occasionally available. However, the price is always expensive.