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Preheat oven to 400°F.
Pierce the potatoes 4 times with the tines of a fork on the top side and arrange on foil-lined baking sheet. Spray potatoes with a little oil and season with salt and pepper. Roast until very tender, about an hour, and let cool enough to handle.
Bring a few inches of water to boil and season with salt. Cook the broccolini or broccoli rabe at low boil to tender, then cold shock in an ice bath, drain and dry it. Finely chop half and chop the rest into florets and bite-sized pieces.
Warm milk with stock, garlic, EVOO and butter and keep at low simmer.
Cut a thin layer of the skin off the top of the potatoes and reserve on foil-lined baking sheet. Gently scoop the flesh of the larger piece of each potato into a bowl. Season inside of scooped potatoes with salt and pepper. Combine half of the warm milk mixture and soft cheese, finely chopped broccolini or rabe and half the cheddar or Gruyere. Depending on the size of your potatoes and how stiff or loose the mixture is, you may or may not need to add all or some more of the warm milk mixture. You are looking for a mixture that is wet, yet firm enough to mound up in the potatoes.
Fill potatoes with the mixture—really mound it up in the potato boats. Top with reserved florets and remaining cheese. Place filled potatoes on foil-lined baking sheet along with the reserved tops and bake until cheese is brown.
To serve, place the thin skin slice on top of each stuffed potato and top with cherry peppers, scallions or chives and a little paprika.