In a medium sauce pan, over medium-low heat, add 12 ounce package of fresh raspberries, sugar, cornstarch, and water. Stir constantly over heat until mixture thickens and sugar is dissolved. Add jam. Stir until completely melted into raspberry filling. Remove from heat and cool.
Preheat oven to 350°. Line two 12 count muffin tins with paper liners.
In the bowl of your mixer add cake mix. Use a wire whisk to whisk cake mix and remove any clumps. Add eggs, oil, water, and buttermilk. Beat on medium speed for 2-3 minutes, scraping bowl down midway.
Fill each cupcake liner 2/3 full. Bake each tray of cupcakes for 14-17 minutes until center springs back when touch. Cool cupcakes completely on baking rack.
Using a special cupcake corer, or large decorating tip turned upside down, remove centers and place cake holes in a separate bowl to use later.
While the cupcakes cool make the Grey Stuff Frosting. In a large bowl combine milk and vanilla pudding. Mix until smooth and mixture thickens. Refrigerate 1-2 hours.
Remove pudding mixture from refrigerator. Fold in cool whip. Add crushed cookies and chocolate pudding. Fold until well combined. Cover and chill 1 hour.
Fill each hold in every cupcake with raspberry filling, about 1-2 teaspoon per cupcake. Place 1 fresh raspberry on top of raspberry filling, in each cupcake center, and gently push down. Top each cupcake with the removed cake holes. Gently push down again. Note: They will stick up a bit, that's okay, the frosting will cover it.
Pipe or spread "The Grey Stuff" frosting on top of each cupcake. Sprinkle with reserved crushed Oreo's. Chill until ready to serve.