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1
Preheat oven to 375 degrees F (190 degrees C). Cut and set aside 25 pieces of plastic wrap about 5 inches square.
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2
For cookies, beat 1/2 cup of vegetable shortening, 2 cups of milk, 2 cups of sugar, the eggs, and 2 teaspoons of vanilla extract together in a large mixing bowl until smooth and creamy. In a separate bowl, whisk the 4 cups of flour with both amounts of unsweetened cocoa, baking soda, and salt until thoroughly combined. Beat the flour mixture into the wet ingredients just until smooth.
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3
Scoop up the batter by teaspoons, and drop onto ungreased baking sheets in small round dollops about 2 inches apart. Recipe should make about 50 cookies. The cookies will rise and expand a lot.
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4
Bake in the preheated oven until the cookies are set in the middle, 8 to 10 minutes. Allow to cool on baking sheets for several minutes before removing to finish cooling on racks.
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5
To make the filling, place 1 cup milk in a microwave-safe measuring cup, and cook in microwave until hot but not simmering, 1 to 2 minutes. Pour the heated milk into a large mixing bowl. Add the cup of room temperature butter, 1 cup of vegetable shortening, 2 cups of sugar, 2 tablespoons of flour, 2 teaspoons of vanilla extract, and the marshmallow creme. Beat the mixture on high speed until the frosting is fluffy, 5 to 10 minutes. At first the frosting will appear lumpy, but keep beating.
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6
To fill the cookies, choose 2 cookies that are about the same size, and spread about 1 1/2 tablespoon of the frosting onto the flat bottom of a cookie. Top with the other cookie, flat side down, and wrap the filled cookie in a sheet of plastic wrap. Place the filled cookie into the freezer. Repeat with remaining cookies and frosting, wrapping each whoopie pie in plastic wrap and freezing.
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7
To serve, remove whoopie pies from the freezer and allow to thaw until very cold but not frozen, 10 to 15 minutes.
