1/2 cup (120 milliliters) olive oil, plus more for drizzling
Crushed red pepper (optional)
Arugula, for plating
Preheat the oven to 375 F (190 C).
Carefully cut off and remove the very tops off the peppers, remove the stems and seeds, and keep the rest of the pepper intact.
In a large bowl, combine the breadcrumbs, anchovy fillets, cherry tomatoes, oregano, garlic, and olive oil and mix to combine.
Using a small spoon, fill the peppers with the breadcrumb mixture until full and packed in, then place on a greased baking sheet. Bake for 25 minutes, turning once, until softened and browned. Remove from oven, transfer to serving plate, then drizzle with olive oil, salt, and crushed red pepper.