Place all 20 Oreos, in a large ziplock bag and use a rolling pin to crush them. I like to crush them just enough to have fine crumbs but still have some bigger pieces.
Add 8 ounces cream cheese,⅓ cup powdered sugar, 1 ½ teaspoons vanilla extract, and 1 dash of salt to a large bowl. Use a hand mixer to beat it until the cream cheese is completely smooth. Fold in 8 ounces cool whip, until fully combined, followed by the crushed Oreos.
Serve with graham crackers, assorted cookies, strawberries, waffle cone pieces, or whatever you want!