Start by preheating your oven to 425°F (220°C). This high heat will help to roast the broccoli quickly and evenly.
Chop the broccoli into small florets and place them in a bowl. Drizzle with olive oil, then sprinkle with salt and freshly cracked black pepper. Toss until the broccoli is well-coated.
Spread the broccoli evenly on a baking sheet lined with parchment paper. Roast in the preheated oven for about 15-20 minutes, or until the broccoli is tender and slightly crisped at the edges. Stir halfway through the cooking time to ensure even roasting.
Once the broccoli is done roasting, it’s time to build your sandwiches. Spread a thin layer of softened unsalted butter on one side of each slice of bread. On the unbuttered side, layer shredded or sliced cheddar cheese, followed by a generous amount of roasted broccoli, and top with another slice of cheese and another piece of bread, buttered side up.
Heat a skillet or griddle over medium heat. Once hot, place the assembled sandwiches in the skillet. Grill for about 3-4 minutes on one side, or until golden brown and the cheese begins to melt. Carefully flip the sandwiches and grill the other side until golden and the cheese is fully melted, another 3-4 minutes.
Remove the sandwiches from the skillet and let them cool for a minute before slicing in half. Serve warm and enjoy the delicious combination of roasted broccoli and melted cheese!