In a large mixing bowl, combine the Oreo instant pudding, powdered sugar, vanilla extract and milk using a handheld or standing mixer. Beat on medium high for about a minute and a half, you will end up with a very thick mixture.
Next, beat in one tub of Cool Whip until it's mostly incorporated. Repeat the same process with the second tub of Cool Whip, until well combined.
Your frosting should become stiffer as you beat it and stand up into peaks on the whisk attachment.
Once all the Cool Whip has been incorporated and the mixture is smooth, your Cool Whip Frosting is ready to use.
You can apply the frosting right away or store it in the refrigerator until you're ready to use it. If you're not using it immediately, be sure to cover it to prevent it from drying out. The longer the frosting is in the fridge, the better it will set up - I recommend chilling for 1 hour at least if you are piping.
Sprinkle on crushed Oreos on top of your cake or cupcakes for added garnish and flavor!
*Important Notes: I recommend only using the brand name Cool Whip. I have tried generic brands of cool whip before and they just don’t work as well. ALSO, be sure the cool whip is not at all frozen. It must be fully thawed or when you go to whip the ingredients together, the consistency will be wrong and won’t stiffen up properly.