Line 8" x 8" pan with 8" wide parchment paper strips, horizontally and vertically, allowing for a bit of overhang.
Split 9 whole graham crackers in half, carefully. Place in a 3 x 3 array on the bottom of the pan.
Whisk pudding, milk and Cool Whip together for about 2 minutes until thickened and showing form.
Spread evenly over graham crackers and place in the freezer to firm up.
Next, mix together the marshmallow fluff and softened cream cheese. Fold in Cool Whip. Spread on top of firmed chocolate layer.
Place the remaining 9 crackers on top in the same 3 x 3 array. Cover with foil and place in the freezer for about 6 hours.
Lift out of the pan using lower parchment paper layer.
Cut out squares along the cracker edges. Trim off any excess along the sides.
Wrap individually in plastic wrap and place them within a large plastic freezer bag. Return to the freezer.
Take out, as needed, and let sit sit for about 5 minutes before eating. Split in half for smaller servings.