Preheat the oven to 375 F.
Coat the potatoes with the olive oil and place on a rimmed baking sheet. Place in the oven to bake for 1 hour, until they are easily pierced with a fork.
While the potatoes are baking, cook your bacon on the stovetop and crumble once cooled.
Remove the potatoes from the oven and set aside to cool. Once potatoes are cool to touch, remove the peels. Add the potatoes to a large bowl, or the bowl of your stand mixer.
Add the butter, sour cream, salt, and pepper to the potatoes, then whip them with an electric mixer or the paddle attachment of your stand mixer. Taste for seasoning and add additional salt and pepper as needed.
Transfer the potatoes to a 10-inch cast iron skillet or an 8x8 baking dish. Top with the cheese and bacon and bake at 350 for 30 minutes, until the cheese is browned and bubbling.