I can't answer for bills, but the first official coins minted in 1793 (the half cent and the cent) each had a different depiction of Lady Liberty. Liberty has had many renditions over the years. The lion's share of all early American coins (into the early 1900s) featured Liberty and a wreath or an eagle, occasionally both. The first US coin to not have Liberty on it was the 1851 three cent coin. The first circulating American coin to have a historical figure was the 1909 Lincoln cent. However, the first commemorative American coin to have a historical figure was the 1892 Columbus half dollar. The only American coin to feature a foreign head of state was the 1893 Queen Isabella Quarter, which was made for collectors.