Preheat oven to 350 degrees F (175 degrees C).
Place garlic cloves in a small baking dish. Drizzle with olive oil, cover, and bake 45 minutes, or until golden brown.
Bring a large pot of lightly salted water to boil. Add potatoes, and cook until tender but firm. Drain, and transfer to a large mixing bowl.
Place roasted garlic, milk, Parmesan cheese, and butter into the bowl with the potatoes. Season with salt and pepper. Beat to desired consistency with an electric mixer.
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