To make the meatloaf: Preheat the oven to 350 degrees F.
Spray the ring mold pan with the nonstick cooking spray, set aside. Slice off the top 1/3 of the head of garlic. Place on a piece of aluminum foil and spray lightly with cooking spray. Place in the oven and roast for 45 minutes.
While the garlic is in the oven, start the meatloaf: Heat the oil in a large skillet over medium heat. Add the onions, celery, and apples, cook until softened, about 5 minutes, stirring occasionally. Transfer the vegetables to a large bowl. Add the remaining meatloaf ingredients and mix well. Place the meatloaf mixture in the prepared ring mold. Bake until cooked through, about 30 minutes.
Meanwhile: make the mashed potatoes: In a large saucepan, cover the potatoes with cold water and add 1 teaspoon of the salt. Bring to a boil over high heat, then lower the heat to maintain a simmer. Cook until fork tender, about 30 to 60 minutes depending upon the size of the potatoes. We've found that boiling the potatoes whole, with the skin on gives the potatoes more potato flavor.
Halve the potatoes crosswise. Put the halves in a ricer cut-side down, and press the potato through the ricer into a bowl. The flesh should easily pass through the holes and the skins remain in the ricer. Discard the skin, and repeat with the remaining potatoes. (Alternatively, peel the cooked potatoes and put through a food mill or mash with a hand-held potato masher.) Immediately add the buttermilk and roasted garlic, to taste, and combine well. Season with the remaining 1 teaspoon of salt and pepper, to taste.
When the meatloaf is done, turn on the broiler. Invert the ring mold onto an ovenproof platter, or, if a baking sheet was used, carefully transfer meatloaf to the platter using a large spatula. Using a spatula, cover the meatloaf on all sides with mashed potatoes, as if frosting a cake. If using a pastry bag, add decorative swirls to the top. Place the platter under the broiler until potatoes are nicely browned, about 12 minutes.
To make the chutney: Combine all the ingredients in a small bowl.
Special Equipment: large ring mold pan, pastry bag and tip (optional) .
*Cooks Note: Yukon gold potatoes have a great buttery appearance when mashed which is a great way to fool the eye when cooking and eating lower fat foods.