Preheat the oven to 425°F. Lightly oil a baking sheet or coat with nonstick spray.
Place potatoes in a large pot and cover with water. Bring to a boil and cook until fork-tender, about 15-20 minutes; drain well.
Place drained potatoes onto the prepared baking sheet. Using a potato masher or the bottom of a glass, carefully flatten each potato to 1/2-inch thickness.
Drizzle with olive oil and season with salt and pepper. Bake until golden brown and crisp, about 25-30 minutes.
While potatoes bake, heat a skillet over medium heat. Add bacon and cook until crispy, about 6-8 minutes. Transfer to a paper towel-lined plate.
Sprinkle baked potatoes with shredded cheddar and bacon. Return to oven until cheese has melted, about 2-3 minutes.
Top with sour cream and chives before serving.