Preheat the oven to 425 degrees F. Place the broccoli on a baking sheet and drizzle it with the olive oil, sprinkle with salt and pepper. You can also use an olive oil spray here! Roast for 15 to 20 minutes, until the broccoli just begins to get golden brown.
While the broccoli is roasting, brush or spray the sourdough slices with olive oil. Once the broccoli is finished, remove the pan from the oven and transfer the broccoli to a boil or plate. Place the bread on the sheet. Bake for 5 minutes, just until it begins to get golden and toasty.
Remove the bread from the oven. Spread the slices all over top with the pimento cheese. Top with the roasted broccoli. Sprinkle on the extra cheddar. Place the sheet back in the oven and bake for 10 to 15 minutes, until melty, golden and cheesy.
Remove from the oven. Sprinkle with some freshly cracked black pepper or even crushed red pepper flakes if you'd like. Serve!