Heat the oven to 425 degrees. Chop off the top of the garlic so that all cloves are "open" and remove some of the outer papery skin.

Fold up a sheet of aluminum foil into a cup-like shape, so the sides come up about 1" and can hold the garlic. If you'd rather use a muffin tin, go for it.

Place the garlic in the foil, cut side up, and pour a little olive oil on top - about 1/2 tbsp. Place the garlic in the oven and roast for about 45 minutes, until the cloves get dark and gooey. Remove the garlic from the oven to cool for a few minutes.

While the garlic is roasting, clean and chop the potatoes. Place in a large pot, cover with water, and bring to a boil. Lower the heat to a fast simmer, and cook for about 15 minutes, until fork-tender.

Strain the potatoes and place back in the pot. Add the milk and butter, and mash with a large fork or potatoes masher. Add more milk if you want smoother potatoes; I like them chunky.

Squeeze out the garlic, and stir in. Serve immediately, topping with salt and pepper as preferred.