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For the cupcakes:
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Preheat oven to 350 degrees F. Line a cupcake tray with 12 baking cups.
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Place one whole Oreo cookie in the bottom of each cup or break apart at least 12 cookies and place the broken pieces into each cup.
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Mix the flour, cocoa, sugar, baking soda, baking powder and salt in a large mixing bowl using a wire whisk. Add the eggs, oil, vanilla and milk and mix well until thoroughly combined. Add the hot water and mix until combined.
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Transfer the batter (it will be very liquid) to a large measuring cup and then pour the batter into each baking cup so it's about three quarters full. You should have a little left over.
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Bake in the preheated oven for 16-18 minutes.
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Makes at least 12 cupcakes
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For the frosting:
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Beat the shortening in a mixer until smooth. Add vanilla and mix until combined. Add the powdered sugar in three additions, scraping down the sides after each addition. Add a Tablespoon of milk at a time and mix together until you achieve the consistency you like.
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Add the cookie crumbs and mix until completely combined. You can add more if you like, but I just wanted a light speckling to show off the white frosting.
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Place frosting in a decorator bag with a tip and swirl the frosting on top of each cupcake. Insert a whole Oreo cookie on top of each cupcake (sticking it into the frosting - see photo).
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You can also apply frosting on each cupcake in a mounded shape. Turn cupcake upside down and roll the top around in a small bowl of cookie crumbs to coat.
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Note: If you choose to pile the frosting on high like I've shown here, you should double this recipe to make sure you have enough.
