Preheat the oven to 400°F.
Halve the head of garlic width-wise then place the bottom half in a piece of foil. Drizzle it with olive oil then sprinkle it with salt and pepper. Add the top of the garlic head back on then securely wrap the foil up and around the garlic. Place it on the center rack of the oven and roast until the cloves are golden brown and soft, 45 to 50 minutes. While the garlic roasts, prep the potatoes.
Peel the potatoes then cut them into quarters.
Bring a large pot of salted water to a boil. Add the potatoes and cook until they are fork tender, about 20 minutes. Drain the potatoes then pass them through a ricer back into the large pot.
Remove the garlic from the oven and squeeze out the cloves onto a plate. Pass the cloves through the ricer into the pot with the potatoes.
In a small saucepan set over medium-low heat, combine the whole milk, heavy cream and butter until warm.
Slowly stream the milk mixture into the potatoes until combined. Taste and season with salt and pepper then serve.