Preheat oven to 400 degrees F. Using a sharp knife, slice the head of garlic in half. Drizzle the olive oil over the exposed garlic cloves and season with salt and pepper. Cover the bulb with aluminum foil and bake for 35-40 minutes. Squeeze the garlic cloves out of their skins and finely mash it with a fork or knife.
Wash, peel, and chop the potatoes into large chunks. Place the potatoes in a large pot and cover them with water. Season with salt.
Cook the potatoes for 18-20 minutes or until fork-tender. Be careful not to overcook the potatoes.
Once the potatoes are fork-tender, place them in a colander and let them sit for 10 minutes.
Place one stick of butter in a saucepan and cook over medium-high heat, stirring frequently. Once it turns a deep amber color, remove it from the heat and place the butter into a bowl. Set about 2 tbsp of brown butter aside.
Heat the heavy cream in a saucepan over medium-high heat for 3-5 minutes.
Mash the potatoes using a potato ricer or potato masher.
Add the heavy cream, roasted garlic, 6 tbsp browned butter, and season with salt and pepper. Mix well.
Garnish with fresh chives and the remaining browned butter. Enjoy!