The original $1,000 bill featured Alexander Hamilton on the front. When someone presumably realized that it might be confusing to have the same former Secretary of the Treasury on multiple denominations, Hamilton's visage was replaced with that of another dead president: the 22nd and the 24th, Grover Cleveland. Like its smaller cousin the $500 bill, the $1,000 bill was also discontinued in 1969. And like the $500 bill, the $1,000 bill would seem to have a lot more use now than it did then.
Why? Inflation, of course! The Consumer Price Index was at 36.8 then, while it's at about 231 today, meaning that a $1,000 bill today would be the equivalent of a relatively modest $159 bill during the Summer of Love. Does it make any sense that we've lost larger denominations as the value of a dollar has gotten progressively smaller? The Treasury argues that keeping the denominations inconveniently small minimizes the possibility of money laundering. This statement could be interpreted as an argument for getting rid of the $50 and $100 bills while we're at it, but that's a topic for a different time.
That being said, hold onto a $1,000 bill that finds its way into your palm even more tightly than you would a $500 bill. There are only 165,372 of the former still in existence.
The Treasury insists that there's no need for bills larger than $100. Canada has halted the printing of $500 and $1,000 bills. The $500 bill is in circulation, while the $1,000 has been withdrawn. However, the $500 note has been around since that currency's inception. As for bills of even larger denominations than $1,000, they enjoyed a brief run in American history before being relegated to memory status.