Preheat oven to 400F.
Drizzle a small amount of olive oil into the bottom of small baking dish or cast iron skillet.
Cut the top quarter or third of the the heads of garlic so the cloves are exposed.
Place the heads of garlic in the baking dish with the roots on the bottom and the cut side on top. You want them to stay upright during the roasting process so make sure they are snug in there. If you are only roasting one or two heads of garlic, crumple up some foil and place in between the garlic heads to keep them upright OR use a smaller dish.
Drizzle the remaining olive oil over the top of the garlic heads and sprinkle with salt and pepper.
Cover the dish or skillet with foil and bake for 40 to 50 minutes. You'll know the garlic is done it is fork-tender and caramelized. You want to see a nice caramel color. If it's not there yet, leave it in the oven for another few minutes before checking again.
Let cool long enough to handle before gently pushing the cloves out. Start from the root and push up just like you are trying to squeeze the last bit of toothpaste out of the tube.
The garlic will be spreadable so use on some toasted French bread, stir into your favorite sauce (so good in Alfredo sauce!) or add to soups.