Recently I made some headway in redeeming the whoopie pie- not in baking a perfect whoopie pie, but it paying homage to it in cookie form.
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These cookies are actually called Homemade Oreos, and I got them from Smitten Kitchen (who has never shared a recipe I didn't like). Hers look like oreos. Perhaps I didn't flatten mine quite enough- but then, I don't think the frosting/filling really mimics the oreo filling well, either.
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In a bowl (of your mixer), combine:
1 1/4 cups flour
1/2 cup unsweetened Dutch process cocoa
1 teaspoon baking soda
1/4 teaspoon baking powder
1/4 teaspoon salt
1 cup sugar [SK's note mentioned that if you make the cookies without the filling, increase the sugar to 1.5 cups, since these chocolate cookies aren't super sweet. I thought they were sweet enough, though]
Stir.
Then cut in
1/2 cup plus 2 tablespoons (1 1/4 sticks) room-temperature, unsalted butter
and
1 egg.
Form 1t-1/2T balls, place on a parchment-lined cookie sheet, and flatten (with your hand, a glass, whatever). Bake for 9-12 min (depending on thickness) at 375F.
Make the filling:
1/4 cup unsalted, room temperature butter
1/4 cup shortening
2 cups powdered sugar
2t vanilla
Beat all that together. Using a spoon (less mess) or a pastry bag with a plain round tip (easy, most mess) or a ziploc bag with a hole cut in the corner (easiest, if you have a plastic bag handy), spoon/pipe the frosting onto an upside-down cookie, then top with another cookie.
Then eat, and be sure to hide a few in your desk drawer, so that when you bring these to your friend's house and everyone devours them instantly, you'll have a few saved.
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