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Step 1
Peel 5 lb. Yukon Gold potatoes (about 10 large), rinsed, patted dry, reserving skins. Cut potatoes into quarters; very thinly slice peels and set aside. Transfer potatoes to a large pot, add 12 garlic cloves, peeled, and pour in cold water to cover. Season generously with kosher salt and bring to a boil. Reduce heat to medium and simmer until a knife easily slides into flesh, 25–30 minutes.
Step 2
Meanwhile, heat ½ cup extra-virgin olive oil in a medium skillet over medium. Add ½ cup (1 stick) unsalted butter and swirl pan until melted. Working in 3 or 4 batches, cook reserved potato skins, stirring occasionally, until deeply browned and crisp, 5–7 minutes. Using a slotted spoon, transfer to paper towels to drain; season with salt. Reserve skillet with any remaining fats. (It’s okay if there are small bits of potato skins left in the oil.)
Step 3
Drain potatoes and garlic; return to pot. Let sit 5 minutes to allow any excess moisture to evaporate from potatoes.
Step 4
Heat ½ cup (1 stick) unsalted butter in reserved skillet with leftover fats over medium until melted and everything is warmed through; set aside.
Step 5
Heat 2 cups heavy cream in a microwave-proof bowl in a microwave until warm, 1–2 minutes. (Or heat in a small saucepan over medium.)
Step 6
Pass hot potatoes (cold potatoes will become gummy) and garlic through a ricer or food mill fitted with fine disk into a large bowl. (Alternatively, you can mash directly in the pot to your desired consistency with a potato masher or fork.) Pour in reserved warm fats and stir to combine. Add warm cream in 3 batches, stirring after each addition until combined before adding more (this will keep your mashed potatoes from getting too loose). Taste mashed potatoes and season generously with more salt.
Step 7
To serve, top mashed potatoes with a few pats of unsalted butter and crispy potato skins; season with freshly ground black pepper.Do ahead: Mashed potatoes and crispy potato skins can be made 1 day ahead. Cover potatoes and chill. Reheat over medium, stirring often and adding ¼ cup milk or low-sodium chicken broth to thin out if needed. Store potato skins airtight at room temperature.