Cut the top of the garlic bulbs off, exposing the cloves. Peel the outer layer of skin off and place garlic on a square of aluminum foil. Drizzle olive oil over the top and wrap the bulb up in the foil. Roast in the oven for 30-35 minutes. Remove from oven, open foil and allow it to cool. Squeeze the garlic out of the skin into a small bowl.
Melt butter in a large skillet over medium-high heat. Add rice and sauté until lightly browned & toasty (about 3 minutes). Add chicken stock and bring to a boil. Cover and reduce heat to medium low. Simmer until rice is tender and liquid is absorbed, about 15 minutes.
Add the garlic, milk and cream cheese. Stir until the cream cheese begins to melt. Mix in the Asiago cheese, salt, and pepper. Stir & cook another 2 to 3 before transferring to a serving dish. Top with additional Asiago and fresh basil, if desired.