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Lies Within Lies

A singer sings this song:

I’m a stockman to my trade, and they call me Ugly Dave.
I’m old and gray and only got one eye.
In a yard I’m good, of course, but just put me on a horse,
And I’ll go where lots of young-uns daren’t try.

He goes on to brag of his skill in riding, whipping, branding, shearing: “In fact, I’m duke of every blasted thing.”

There are two fictions here: The singer is pretending to be Ugly Dave, and Ugly Dave is telling boastful lies. But why doesn’t this collapse? How are we able to tell that the fictional Ugly Dave is lying (which is essential to the song’s meaning), rather than telling the truth?

“We must distinguish pretending to pretend from really pretending,” writes David Lewis in Philosophical Papers. “Intuitively it seems that we can make this distinction, but how is it to be analyzed?”