The box contains 8 bills total, so picking two without replacement gives 8·7 = 56 distinct outcomes in the sample space, all of equal probability.
Of those 56 outcomes, the only outcomes that yield a sum ≤ 16 are picking a $5 bill 1st and a $10 bill 2nd or a $10 bill 1st and a $5 bill 2nd: 1/8·4/7 + 4/8·1/7 = 8/56.
P(X > 16) = 1 - 8/56 = 48/56