Prepare the Meatloaf: Preheat your oven to 375°F (190°C). In a large bowl, combine ground beef, onion, garlic, breadcrumbs, egg, milk, Worcestershire sauce, ketchup, oregano, basil, salt, and pepper. Mix until just combined—do not overmix.
Form the Meatloaf: Shape the mixture into a loaf and place it on a baking sheet or into a loaf pan. Bake for 40–45 minutes, or until the internal temperature reaches 160°F (71°C). Let the meatloaf rest for 10 minutes before slicing.
Bake or Microwave the Potatoes: While the meatloaf is cooking, scrub the potatoes and pierce each one several times with a fork. Bake in the oven for 45 minutes, or microwave on high for 8–10 minutes until tender.
Make the Loaded Filling: Cut the cooked potatoes in half lengthwise and scoop out the flesh into a mixing bowl. Mash with butter, sour cream, salt, and pepper. Stir in cheddar cheese and chopped green onions.
Stuff and Bake: Spoon the mashed potato mixture back into the potato skins and sprinkle with extra shredded cheese. Bake for 5–10 more minutes until the cheese is melted and bubbly.
Serve: Plate the sliced meatloaf with the loaded potato halves and garnish with extra green onions or a dollop of sour cream, if desired.