Place oreo cookies in a ziplock bag and crush finely with a rolling pin (or give them a quick whirl in the food processor). Pour into a pie plate and add melted butter. Stir to combine. Place in the freezer for about 15 minutes.
Roughly chop chocolate pieces. Add 1/2 cup whipping cream to a small sauce pan and heat until it just starts to bubble. Add chocolate to a bowl and pour whipping cream over and stir until chocolate is melted and smooth. Pour over cookie crust. Place in freezer for about 15-20 minutes or until chocolate is set.
Add softened cream cheese and dulce de leche to a mixer bowl and beat on medium speed until smooth and well combined. Slowly add 2 cups of whipping cream at low speed until combined. Stop mixer and scrape down the sides of the bowl. MIx on medium-high for about 2 minutes or until mixture is fluffy. Pour over fudge layer. Top with cool whip or whipped cream. Cover and refrigerate or freeze until ready to serve.
If frozen, remove pie about 20 minutes before slicing. Drizzle with chocolate and caramel sauce if desired.