Preheat the oven to 350 degrees. Prepare two muffin tins with baking cups. Spritz the baking cups with nonstick cooking spray.
Whisk together the flour, baking powder, and salt. Set aside.
In a mixer, beat the butter and sugar until fluffy, about 6 minutes, scraping down the sides as needed.
Mix in the eggs and vanilla, blending well.
Add the flour mixture a little at a time, alternating with the milk, until just blended. Stir in the cookie crumbs.
Using a large scoop, fill the cupcake liners two-thirds full.
Bake the cupcakes for 20 to 22 minutes or until a toothpick in the center returns clean.
Place the muffin tins on a wire rack to cool for 10 minutes prior to removing the cupcakes to cool completely.
Frosting
Sift together the cocoa and powdered sugar. Stir in the salt and set aside.
Beat the butter on high for 3 to 5 minutes or until creamy and light in color. Mix in the vanilla.
Add the sugars and whipping cream, beating on low until the sugar is incorporated and then switching to high speed and scraping down the sides as needed.
Transfer the icing into a decorating bag with a round tip and frost with a back and forth pattern across each cupcake.
Decorations
For the ears, cut each Tootsie Roll midgee in half. Roll and squeeze the candy to soften and shape into an owl ear.
For the eyes, twist the mini Oreos releasing one cookie so that the cream sticks on one side. To the cream, press a chocolate chip against the white cream.
Arrange the coconut on the cupcakes in an inverted V-shape. At the top of the V, add an M&M and press one eye on each side of the M&M. Then, press an ear under each eye.
To finish, allow the icing to set and lightly dot the icing with a fork.