Heat the oven to 375 degrees F/190 degrees C.
Cut the pepper in half lengthwise, remove the seeds leaving the stems intact and place in a small baking dish. Spread a spoonful of tapenade on the bottom of each pepper. Lay 4 basil leaves in each half, then 2 tomato quarters in each half, seed side up. Scatter over the sliced garlic. Drizzle with olive oil and sprinkle with salt and pepper. Bake until the pepper is completely soft and getting dark around the edges, about 1 hour. Serve with crusty bread.