1 can sweetened condensed milk
8 ounces bittersweet chocolate
1 pint heavy cream, divided
6 ounces Oreo cookies – about 25 cookies
5 tablespoons melted butter
1 – 10 ounce package bittersweet chocolate chips
1 cup peanut butter
8 ounces cream cheese, softened
Peel the label off the can of sweetened condensed milk. Place in a saucepan and put water in the pan to cover the can with 1 to 2 inches water. Bring water to a boil and then turn the heat to low and simmer for 1 1/2 hours (checking regularly to ensure that the water completely covers the can at all times). Turn the can over and simmer for another 1 1/2 hours. Remove can and let cool completely before opening. (You can also make this in a slow cooker – 8-10 hours on low).
Place the bittersweet chocolate in a heatproof bowl. Bring 1 cup of the cream to a boil in a small saucepan over medium heat. Immediately pour the boiling cream over the chopped chocolate. Tap the bowl on the counter to settle the chocolate into the cream, then let it sit for 1 minute. Using a rubber spatula, slowly stir until all the chocolate is melted and the mixture has emulsified. Place the ganache in the refrigerator until it has cooled and thicken (no more than 2 hours).
Scrape off the cream filling from the Oreo. Place Oreo cookies sans cream filling into a food processor and pulse until it make crumbs. Pour in butter and pulse to combine. Press the cookie crumbs into the bottom of a deep dish pie pan.
In a double boiler, melt the dark chocolate chips. Add in the peanut butter and stir until combined. Add melted chocolate chips and peanut butter, cream cheese and 1 cup whipping cream together in a stand mixer. Beat until thick and fluffy, about 3-5 minutes.
Spread almost all of the ganache over the Oreo crust. Reserve 2 tablespoons for drizzling on the top of pie.
Spoon chocolate peanut butter mixture into the pie crust over the ganache layer.
Drizzle half the can of sweetened condensed milk dulce de leche over the chocolate mixture. Reserve remainder for another use. Drizzle extra ganache over top.
Refrigerate overnight or place pie in freezer for at least 1 hour before serving.