Preheat oven to 375 F. Poke holes in potatoes and rub with olive oil. Place onto a baking sheet and bake for one hour, or until fork tender. Let cool.
When potatoes are cool enough to handle, slice the tops off of potatoes and scoop out the potato filling.
Place potato filling in a bowl and mash with butter, milk, salt, pepper and 1/2 cup shredded cheddar cheese. Spoon the filling back into the potato shells and sprinkle with the remaining 1/2 cup shredded cheddar cheese.
Bake for another 20-25 minutes.
