Preheat oven to 325 degrees.

Cut tomatoes in half horizontally. Place cut sides up onto a baking sheet. Drizzle with oil and sprinkle with pepper.

Bake until tomatoes collapse and begin to caramelize, 2 to 3 hours. Spread garlic on tomatoes about halfway through baking cycle.

When done, remove from heat, sprinkle with basil and serve hot, or allow to cool slightly before serving.