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Origin documented
“A pretty penny”
What it means
A large sum of money.
Where it comes from
The understatement is the joke. Naming the smallest common coin to describe a substantial expense has been amusing English speakers since at least the eighteenth century.
How sure are we?
Pretty in the older sense of considerable, rather than attractive. The same sense survives in a pretty pass and a pretty state of affairs, neither of which is complimentary.