Rub olive oil, salt, and pepper on each potato and place in a cast-iron-skillet to cook for 30 minutes.
Once finished remove from oven. Using the bottom of a small bowl, gently smush each potato until in flat-like shape.
In a large mixing bowl, mix together cream cheese, mayonnaise, 1 cup of Monterrey Jack cheese, parmesan, garlic, crabmeat, onion, and Worcestershire sauce. Season to taste with salt and pepper. Transfer to cast-iron-skillet covering potatoes. Top mix with remaining Monterrey Jack cheese. Add more if desired.
Bake for 15-20 minutes until cheese is bubbling and a few brown spots.