1. Combine Oreo crumbs and melted butter.
2. Place cupcake liners in a cupcake pan and about about 1 tbsp of Oreo mixture to each liner. Pat down to form the crust.
3. Combine cream cheese, milk and sugar in a bowl and mix with a mixer until smooth and creamy.
4. Add the dry cheesecake flavored pudding mix and mix until well combined. Mixture will be thick and sticky.
5. Fold in 8 oz of the cool whip. NOTE: Because the cream cheese mixture is thick and sticky, it might seem to curdle a bit, but keep mixing – it will come together.
6. Add ice cream mixture to cupcake liners and put in freezer.
7. Add the raspberry jam to the remaining 4 oz of Cool Whip and mix until smooth with a spatula.
8. Remove cupcakes from freezer and add raspberry Cool Whip on top.
9. Place cupcakes back in freezer until frozen.