Bring about 1 inch of water to a simmer in a medium saucepan. Put the chocolate in a medium heatproof bowl. Set the bowl over the saucepan, making sure that the bottom of the bowl does not touch the water. Let the chocolate sit until melted and smooth, stirring occasionally. Remove from the heat.
Meanwhile, put the cookies in a food processor and process until finely ground (you should have about 1 1/2 cups crumbs). Pour the cookie crumbs into the chocolate. Add the figs, confectioners' sugar, bourbon, condensed milk and vanilla and stir until well blended.
Cover and refrigerate the mixture until firm enough to roll into balls, about 45 minutes. Spread the granulated sugar in a shallow bowl. Scoop about 1 tablespoon of the mixture and shape into a smooth ball and then roll in the granulated sugar. Serve at room temperature.
Store the balls in an airtight container in the refrigerator for a week or in the freezer for up to 1 month.
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