Let's not limit our new bills to $1 or some random round number.
$69 bill: Clinton, obviously
$2.5 bill: Kennedy (shot twice, missed once)
$1,000,000,000,000 bill: Wilson, in honor of creating the Federal Reserve
2¢: Carter, because everyone gets pissed when he gives his.
94.5¢ bill: Truman, because that's the current Yen/Dollar exchange rate. This will require daily re-printings
all I've got at the moment