Preheat oven to 400F. Cut off the top of the head of garlics to expose the cloves and place in the center of a piece of aluminum foil. Drizzle olive oil over the cloves and wrap in the aluminum foil. Place on a baking sheet and roast for 30-40 minutes or until the garlic is softened. Set aside to cool to room temperature.
In a small mixing bowl, add the butter, Parmesan cheese, fresh parsley, salt and pepper. Squeeze in the cooled roasted garlic and mix everything together to combine. Set aside.
Place down the slices of bread on a clean surface and spread an even layer of the garlic butter over the top.
Heat up a skillet over medium heat. Working quickly, place down a slice of bread buttered side down. Top with a slice of American cheese, 1/2 cup of the shredded cheese and another slice of American cheese. Place a slice of bread over the cheese filling buttered side up.
Toast the bread for 2-3 minutes and then flip to toast the other side of the sandwich for 2-3 minutes or until golden brown and the cheese is fully melted. Repeat with remaining ingredients for a total of (2) sandwiches.
Serve sandwiches immediately on its own or with tomato soup. Enjoy!