What is a 5 bill worth with an Indian head on it?

A $5 bill featuring an Indian Head design typically refers to the Indian Head gold $5 coin, minted from 1908 to 1929. The coin's value is primarily based on its gold content and collectible demand, often ranging from several hundred to over a thousand dollars, depending on its condition and rarity. If you meant a paper currency bill, the Indian Head design is not used on modern $5 bills, which feature different designs. Always consult a numismatic expert for precise valuation.