Sugar Cookie Layer: Place cupcake liners in a cupcake/muffin pan. Press about 1 tablespoon of premade cookie dough to each cup.
Cupcakes: Beat together the eggs, cake mix, melted butter, sour cream and buttermilk on low for 30 seconds, then on medium speed for 1-2 minutes. Use a cookie scoop to add 3 tablespoons of cake batter over each sugar cookie.
Bake the cupcakes at 350 degrees for 20 minutes, or until a toothpick inserted comes out clean. Allow the cupcakes to cool in the pan for 5 minutes before transferring to a cooling rack.
Cupcake Filling: Use a knife or cupcake corer to remove the center of each cupcake. Save the cupcake middles for later. Add the raspberry jam to a ziplock bag and pipe the filling into each cupcake hole.
The Grey Stuff: In the bowl of a stand mixer with a whisk attachment, add the heavy cream, white chocolate instant pudding mix, and OREO cookie crumbs. Whip on high until stiff peaks are formed. Add the Grey Stuff to a large piping bag with a large star tip. Using a circular motion, pipe the Grey Stuff onto the cupcakes.
Toppings: Immediately after piping on the Grey Stuff, add a few grey and white pearl sprinkles, if desired. Break up the cupcake middles, reserved from earlier, into small crumbs and sprinkle over the tops of the cupcakes.