Preheat the oven to 400 degrees. Line a large baking sheet with parchment paper or aluminum foil.
Brush the olive oil all over the outside of the potatoes and then season the skin with salt and black pepper.
Transfer the potatoes to the prepared pan. Bake for 1 hour, or until fork tender. Keep the oven at 400 degrees. Let the potatoes stand until cool enough to handle (this is a great time to cook the bacon).
When cool enough to handle, peel 1 potato completely and discard the skin. Transfer the flesh to a large bowl.
Using a sharp knife, slice into the four remaining potatoes, lengthwise from end to end, and about 1/4 of the way down. Using a small spoon or melon-baller, scoop the flesh from the potatoes, leaving a 1/4-inch-thick layer of flesh with the skin. Transfer the flesh to the bowl with the first potato.
Return the potato shells to the baking sheet.
Using a handheld masher or fork, mash the potato pulp until smooth. Add 1 cup of the cheddar cheese, sour cream, heavy cream, butter, 1/2 teaspoon salt, and 1/4 teaspoon black pepper. Mix until smooth. Fold in the bacon and 1 tablespoon of the chives.
Spoon the potato mixture back into the potato shells. Top with the remaining 1 cup of cheddar cheese.
Return the pan to the oven and bake for 12 to 15 minutes, until the potatoes are heated through and the cheese melts.
Top with the remaining chives and serve hot.