1/2 cup granulated sugar, plus more for sprinkling
1 teaspoon kosher salt
1 teaspoon anise seed
2 packets dry yeast
1/2 cup whole milk
1/2 cup water
8 tablespoons unsalted butter (1 stick)
4 large eggs
4 1/2 cups all-purpose flour
1 egg yolk beaten with 2 teaspoons water
How to make it
In a small mixing bowl, combine sugar, salt, anise seed, and yeast.
Heat milk, water, and butter in a small saucepan over medium heat until butter is just melted; do not allow it to boil. Add milk mixture to dry mixture and beat well with a wire whisk.
Stir in eggs and 1 1/2 cups of the flour and beat well. Add remaining flour, little by little, stirring well with a wooden spoon until dough comes together.
Turn dough out onto a lightly floured wooden board and knead for 9 to 10 minutes until it is smooth and elastic, and no longer sticky. Place dough in a lightly oiled bowl, cover with a clean kitchen towel, and allow it to rise in a warm area until it has doubled in size (about 1 1/2 hours).
Heat oven to 350°F. Punch down dough and divide into 2 pieces. Cut 3 small (1-ounce) balls from each half and mold them into skull-and-bones shapes. Shape large balls of dough into round loaf shapes, and place skull-and-bones on top. Place breads on a baking sheet lined with parchment paper and let rise another hour.
Brush loaves with egg yolk mixture and bake at 350°F. Halfway through baking, about 20 minutes, remove loaves from oven and brush again with egg wash and sprinkle lightly with granulated sugar. Return to oven and bake until loaves are golden brown and sound hollow when tapped, about another 20 minutes.