According to the US Treasury Department, the largest currency denomination ever printed by the Bureau of Engraving and Printing was the $100,000 series 1934 gold certificate, which featured a portrait of President Woodrow Wilson.
But you couldn't find these in, say, J.P. Morgan's wallet. A limited number were printed at the end of 1934, and they were intended for government use only. By the end of that year there were several other big bucks, including denominations of $500, $1,000, $5,000, and $10,000. These were perfectly legal tender, but mostly used for bank transfers.
Production of these bills stopped around 1946, and in 1969 the government decided to cease using them altogether. The big bills are still around (though mostly in the hands of collectors), and can be used to make a down payment on a plasma TV. However, the U.S. government has made an effort to pull them out of circulation.
The biggest bill still in use is the classic C note -- the $100 bill. The Benjamin was the highest note to survive the 1969 repeal, because by that point electronic money transfer systems had rendered large paper bills unnecessary
