The classic New York-born black and white cookie is given a healthy upgrade with the addition of Colavita Extra Virgin Olive Oil, which replaces the butter, imparting a nutty and bright flavor to the cookie base. The cookies are topped with half vanilla and chocolate icing, made with Perugina 70% Cacao Bittersweet Chocolate, swirled with a touch more olive oil for a silky texture.
Position 2 racks in the middle of your oven. Preheat the oven to 375 degrees F. Line two baking sheets with parchment paper.
In a medium bowl, sift together the flour, baking powder, and salt.
In the bowl of a stand mixer fitted with the paddle attachment, combine the Colavita Extra Virgin Olive Oil and sugar. Mix on low speed until the mixture is combined and like wet sand in texture. Beat in the eggs one at a time. Stir in half of the flour mixture, then stir in the milk mixture, and then the rest of the flour mixture; beat it all until the batter is smooth. Use a rubber spatula to scrape down the sides of the bowl.
Drop the dough by rounded tablespoonfuls on to the prepared sheets, leaving 2 inches around each cookie to allow for some spreading.
Bake for 8-12 minutes, rotating the pans at the 5 minute mark, or until the cookies have a dull appearance but are just barely “set” in the centers. Remove, and let cool on the baking sheets for a few minutes before transferring to wire racks to cool completely.
While the cookies cool, making the icing(s). To make the vanilla icing, combine the confectioners’ sugar, lemon juice (if using), vanilla, and 2 tablespoons of water. Whisk until combined. If the mixture remains too thick, continue adding water, 1 teaspoon at a time, until it has reached a thick but spreadable consistency.
To make the chocolate icing, melt the chocolate in the top of a double boiler or in the microwave. Once melted, whisk in the olive oil and stir until completely combined.
When you’re ready to ice your cookies, place them so that the flat (bottom) side is facing up.
Using a spoon, spread the vanilla frosting on the cookies first, covering slightly more than half of the cookie (the opaque chocolate will cover it up along the center). Let the icing set for a few minutes, and then spoon and spread the chocolate icing along the remaining half of the cookies, so that there are even portions of vanilla and chocolate icing on top of each cookie. Let the cookies “set” until the icing is firm, and then serve.