Heat oven to 350°F. Prick cut sides of spuds with a fork. Rub all over with oil. Place cut-side down on a sheet pan.
Bake for 35 to 40 minutes or until just tender. Let sit 15 minutes.
Carefully scoop flesh from potatoes, leaving shells intact. Mash potato pulp, cream cheese, and sugar with a potato masher until smooth. Season with salt and pepper. Spoon or pipe mixture into shells. (To make ahead, cover and chill for up to 2 days. Let stand for 15 minutes before baking.)
Bake potatoes 25 to 30 minutes more or until golden and thoroughly heated. Serve with bowls of desired toppings.