Crush the Oreo cookies and mix with melted butter. Press this mixture into the bottom of a 9x13 inch dish to form the crust.
In a mixing bowl, combine the chocolate pudding mix, 1 cup of milk, and whisk until smooth. Fold in ½ cup of Cool Whip and spread this mixture over the crust.
In another bowl, beat the softened cream cheese, sugar, and vanilla extract until smooth. Fold in the remaining Cool Whip and spread this mixture over the chocolate layer.
In a small bowl, mix the remaining 2 tablespoons of milk with the raspberries. Spread this mixture over the cream cheese layer.
Chill the dessert in the refrigerator for at least 2 hours before serving.
Notes
For a firmer dessert, let it chill overnight. You can also use different fruits for variation.