$500 - Wiliam McKinley
These are from the last series (all printed from 1934–45) of large US currency to be in public circulation. These are all still legal tender, and several hundred of each denomination are still around (mostly in the hands of private collectors). This is money for people with a lot of money.
$1,000 - Grover Cleveland
The Federal Reserve began taking them out of circulation in 1969—though this process can only occur when someone deposits the bill at their bank.
$5,000 - James Madison
You can still deposit these at your bank (if you ever get your hands on one), though you will have to jump through some hoops. Typically these bills are sold these days for far greater than their face value, as people like to collect them.
$10,000 - Salmon P. Chase
This guy was not president. He was a senator and governor from Ohio, Treasury Secretary under Lincoln, and eventually Chief Justice of the Supreme Court.
$100,000 - Woodrow Wilson
This bill was never in public circulation, they were used in formal transactions between Federal Reserve Banks. Introduction of the electronic money system made large cash transactions obsolete.
