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Washington's portrait was first used on the 1869 series of $1 United States Notes. That series was replaced with other designs featuring other notable individuals. The current portrait was placed on $1 bills starting in 1918.
If you're referring to any denomination and not just $1 bills, the first federally-issued bills featured two different individuals: $5 Demand Notes of 1861 carried a portrait of Alexander Hamilton. $10 Demand Notes had a picture of Abraham Lincoln. $20 Demand Notes had images of allegorical figures rather than actual persons
The US government issued $5,000 bills at four different points in history, but denominations over $100 were removed from general circulation in 1969. The most recent Federal Reserve Note (2 issues, 1934) is still legal tender. 1840 Second Bank of the United States 1882 Gold Certificate (National Bank Notes and Treasury Notes) 1914 Federal Reserve Note, portrait of James Madison, National Stability era 1934 Federal Reserve Note, portrait of James Madison, World Standard, two versions issued
1976 and later (green-seal notes): a partial reproduction of John Trumbull's famous painting depicting the signing of the Declaration of Independence. Up to 1963 (red-seal notes): a picture of Thomas Jefferson's home, Monticello. Thomas Jefferson's portrait is on the front of both types of bill. Note that all current American bills have captions on them identifying the person pictured on the front and the scene or building on the back.
No one was on those bills because they don't exist. The only $500 bills printed in those series were issued as Federal Reserve Notes; both carried a portrait of President William McKinley. The last $500 silver certificates were printed in 1878.