20Oreosgluten free or not, depending on preference
Put a standard loaf pan in the freezer to chill.
Divide 20 Oreos into two groups of 8 and one group of 4. Scrape the filling off of 8 sandwiches (save it!) and crush the cookies into a fine crumb. A food processor is the best tool for this, but a coffee grinder or rolling pin and ziplock bag will also work. Use a sharp knife to cut the next 8 sandwiches into small chunks. DON'T remove the filling. Cut the other 4 sandwiches into fourths and set aside.
In a large bowl, whisk the condensed milk, filling and vanilla extract until mostly smooth.
Mix in the Oreo crumbs and chunks.
Use a stand or hand mixer to whip the heavy cream until stiff peaks form. Gently fold the cream into the cookie mixture until completely combined.
Pour into the chilled pan, and top with the larger Oreo pieces. Chill in the freezer for 4 to 6 hours before serving. (I also recommend letting it set in the freezer for at least an hour before covering.) Enjoy!