Preheat your oven to 400°F (200°C). Cut the top off the garlic head to expose the cloves, drizzle with 1 tablespoon olive oil, wrap in foil, and roast for 30-35 minutes until soft and golden. Your kitchen will smell like heaven, and your neighbors might "coincidentally" drop by.
While the garlic is doing its thing, wash your potatoes and cut them into 1-inch chunks. Leave the skin on for rustic vibes (and because peeling potatoes is tedious and life is short).
Place potatoes in a large pot, cover with cold water, add a generous pinch of salt, and bring to a boil. Cook for 15-20 minutes until fork-tender.
Drain the potatoes thoroughly. No one wants watery mashed potatoes. That's just sad potato soup.
Return potatoes to the pot and let them steam dry for about 2 minutes. This step seems pointless but makes a difference—trust me.
Squeeze the roasted garlic cloves out of their papery skins into the pot with the potatoes. They should be soft like butter and smell divine.
Add butter and mash everything together while the potatoes are still hot. The butter needs to melt completely and make everything gloriously rich.
Pour in the warm milk/cream gradually while continuing to mash until you reach your desired consistency. Some like it chunky, some like it smooth—I'm not here to judge.
Fold in the chopped rosemary, salt, and pepper. If using Parmesan, add it now and stir gently.
Taste and adjust seasonings because you're a chef now. Drizzle with the remaining olive oil before serving to look extra fancy.