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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

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Q: Who was the first person to have his face on a US dollar bill?
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