Put your ice cream freezer bowl in the freezer for at least 12 hours, but preferably 24 hours before making this recipe.
Add most of the Oreo cookies package to a zip lock bag and let out all of the air and seal. Using a rolling pin, crush the Oreo cookies. (Reserve some of the Oreo cookies for ice cream toppings.)
In a mixing bowl, add the heavy cream, condensed milk, and vanilla extract and whisk together until well combined.
Place the Metal Loaf pan in the freezer so it's nice and cold when we add the prepared oreo ice cream to it later.
Turn on the ice cream maker; add the paddle, pour the mixture into the frozen freezer bowl, and let mix until thickened about 20 minutes, but I find mixing it for 30 minutes gives perfect, fluffy ice cream. The ice cream will have a soft, thick, creamy texture.
At the end of the churning process, add the crushed Oreos. Let the ice cream continue to churn until all of the Oreos are combined into the ice cream mixture.
Scoop the cookies n cream ice cream into the frozen metal loaf pan. Top with more whole Oreos and press the oreo cookies into the top of the prepared frozen oreo ice cream.
Seal with saran wrap and place in the freezer for two hours or longer to firm up even more.