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Preheat oven to 375F. Slice off the top half-inch of the bread and reserve. Scoop out the insides of the loaf so the shell's about a half-inch thick and cut the scooped bread into cubes.
In a large skillet, heat 6 tablespoons olive oil over medium heat. Add garlic and rosemary, and cook 2 minutes. Place the bread shell on a baking sheet and brush the inside with some of the seasoned oil.
Add 3 cups bread cubes to the skillet with the remaining seasoned oil and toss to coat. Transfer cubes to the baking sheet, scattering them around the bread shell. Place the reserved bread top on the baking sheet cut side up. Bake until everything's brown and toasted, 10-15 minutes.
Meanwhile, in the same skillet, heat the remaining 2 tablespoons olive oil over medium-high heat. Add the onions and cook, stirring until golden, 10 minutes and transfer to a bowl. Add the steak to the skillet and cook 4 minutes; season with salt and pepper. Add wine and cook for 2 minutes. Stir in the reserved onions.
Spoon half of the steak-onion mixture into the toasted bread bowl. Top with half of the cheese, then half of the croutons. Layer with the remaining steak-onion mixture, croutons and cheese.
Bake until the cheese has melted, 3-5 minutes. Top with the bread lid. Slice into wedges and serve.