Start by crushing Oreo cookies in a food processor until they resemble fine crumbs. In a mixing bowl, combine the crumbs with melted butter, then press the mixture firmly into the bottom of a 9x13 dish. Refrigerate for about 15 minutes to set.

In a medium bowl, whisk together the chocolate pudding mix and milk until fully combined and smooth. Whisk until the mixture thickens, typically about 2 minutes. Set aside for a minute.

In a separate bowl, beat the softened cream cheese and powdered sugar together using an electric mixer until creamy. Gently fold in the Cool Whip. Ensure it’s mixed thoroughly.

Begin layering by spreading half of the cream cheese mixture over the crust. Pour half of the chocolate pudding over this layer and smooth it out. Scatter a layer of raspberries on top. Repeat with remaining layers.

Dollop and swirl extra Cool Whip over the top layer. Cover tightly with plastic wrap and refrigerate for at least 4 hours, preferably overnight.