There were several versions of the $500 bill, featuring a portrait of President William McKinley on the front. The last $500 bill was printed in 1945 and it was formally discontinued in 1969. Today both the $500 and the $1,000 bill are worth more than its face value because of their rarity. It remains legal tender, but most of them are in the hands of dealers and collectors.
The original $1,000 bill featured Alexander Hamilton on the front, but he was replaced by Grover Cleveland to avoid confusion because Hamilton was originally on the $2 bill. The $1,000 bill was discontinued in 1969. There are only slightly over 165,000 bills with Cleveland's picture on them still in existence.
The $5,000 bill was initially issued to finance the Revolutionary War and was only officially printed when the Civil War began and it had James Madison's picture on it. President Nixon ordered that the bills be recalled in 1969 due to fear of criminals using them for money laundering activities. Fewer than 400 are believed to exist.
Salmon P. Chase was never president, but he was a governor and senator from Ohio, he served as Secretary of the Treasury under Lincoln and became chief justice of the Supreme Court. He was on the $10,000 bill which was the largest denomination ever printed for public use, but it never got much use. That's because during the time it was in circulation it was worth more than the net worth of the average American. The bill was first printed in 1918 and was part of the 1969 purge. Only a few hundred of them have survived.
Woodrow Wilson was on the $100,000 bill which was actually a gold certificate and it was never circulated or issued for public use. They were created during the Great Depression in 1934 and used for conducting official transactions between Federal Reserve banks. Only 42,000 were ever printed. These bills can not be legally held by collectors, but some institutions display them for educational purposes.
Some think the $500 and the $1,000 bills should be brought back because of inflation. In 1969, the Consumer Price Index was at about 36.8. In 2019, it was at over 256. That means that today a $1,000 bill would be the equivalent of only $153 in 1969 because the value of a dollar has gotten progressively smaller! The Treasury's argument is that keeping the denominations inconveniently small minimizes the possibility of money laundering.