Crush your Oreo cookies in a plastic bag with a rolling pin or in a food processsor. Mix the crumbs and melted butter with a fork in a medium sized bowl. Press into a 9” pie plate and chill until ready to fill.
Melt the baking chocolate in a medium sized bowl according to package directions for melting. Typically, chocolate will take about 1-2 minutes on high power, but make sure you stir every 30 seconds.
Stir 1/2 of the can of sweetened condensed milk (about 5 ounces volume) into the melted chocolate. Stir in 1 teaspoon of vanilla extract. Let sit for a few minutes, but be sure to stir it occasionally so it doesn’t turn into fudge.
Stir the remaining sweetened condensed milk in another medium bowl with the peanut butter and 1 teaspoon vanilla. Stir until smooth.
Whip the heavy whipping cream on high speed until stiff peaks form, adding in the powdered sugar and 1 teaspoon of vanilla extract while it’s mixing.
Stir 1 cup of the whipped cream carefully into the peanut butter mixture. Fold carefully so you don’t break the cream. Spread in the bottom of the prepared crust.
Stir up the chocolate mixture until it’s smooth. Fold in 1 cup of whipped cream carefully so you don’t break the cream. Spread on top of peanut butter layer.
Top with remaining whipped cream and chocolate shavings. (Chocolate shavings can be made by using a potato peeler on an ounce of chocolate.)
Chill for at least 4 hours or overnight before cutting. Store loosely covered in the refrigerator and eat within 3 days.