Peel garlic cloves and place them into a small sauce pan with olive oil. Bring to a boil and then reduce heat to low until garlic begins to brown. Remove from heat and set aside.
Add potatoes to a large pot and fill pot with water, just enough to cover the potatoes. Salt the water. Cover and bring water to a boil. Once boiling, remove cover and cook for another 15 to 20 minutes, or until potatoes are very tender.
Remove garlic from oil and potatoes from water and place into bowl of stand mixer. Do not discard oil or water since we will use them later. Pulse mixer with paddle attachment to mash the potatoes and garlic together. If you don't have a stand mixer, simply use a potato masher to achieve this.
Once potatoes and garlic are mashed, add reserved olive oil, heavy cream, 1 or 2 teaspoons of salt (to taste), 1 teaspoon pepper, and 3/4 cup of reserved potato water. Mix on low to combine, or use a wooden spoon to combine. If potatoes are too dry, add a little more water until desired consistency is reached. Place in serving dish and serve immediately.