Preheat oven to 375F.
Line a rimmed baking sheet with parchment paper. In a small bowl, soak the bread pieces in the milk.
Heat EVOO, a turn of the pan, in a medium skillet over medium to medium-high heat. Add celery, onion, carrot and garlic, season with salt and pepper, and saute to soften, 10 minutes, stirring frequently. Pour in sherry and stir. Let reduce by half. Turn off heat and let cool.
Meanwhile, place ground beef in a bowl and add cheese. Wring out the bread and add it to the meat, crumbling it into small crumbs over the bowl. Add cooled veggies and season with salt, pepper, mustard, cayenne and Worcestershire. Add eggs then mix with your hands to combine.
Form meat into a log-shape loaf, about 10 inches long, on a parchment-lined baking sheet. Bake for 40-45 minutes. Make mashed potatoes while meatloaf cooks.
Place potatoes in a pot, cover with water and bring to boil. Salt water and cook to tender. Drain and mash with half-and-half or cream, salt, butter, egg yolks and season with pepper. Transfer to a pastry bag fitted with a star tip.
Pipe the mashed potatoes in a decorative fashion to cover the loaf completely. Sprinkle the top with a little paprika and transfer back to oven for 15-20 minutes or until lightly browned (to give it a "bark" look).
Place roasted mushrooms around the base and decorate with fresh bay leaves and cranberries.
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