A 1000 dollar bill looks like Grover Cleveland, the 22nd and 24th President of the United States on the front. He is the only President who did not serve two consecutive terms. The $1000 bill design captured Grover Cleveland's portrait in 1934 series. An older $1000 bill's design in 1918 was that of Alexander Hamilton. Large bills such as $1000 to $10,000 are no longer used as legal tender effective 1969.