First, peel the tomatoes: your pappa al pomodoro will be much more velvety and you won't find the tomato skins underneath your teeth. Plunge the tomatoes for 30 seconds in a pot of hot boiling water, then move them with a slotted spoon into a bowl of cold water. This will help you skin the tomatoes. Once peeled, collect the tomatoes in a bowl and squash them with your hands.
Cover the bottom of a pot with extra virgin olive oil, add the finely chopped garlic and dried chili pepper, according to your taste. Cook te garlic on low flame until fragrant and golden, then add the peeled tomatoes. Cook the tomatoes on low heat for about twenty minutes, until they start to collapse into a sauce.
In the meantime, dip the slices of stale bread in cold water. When they have soaked up enough water to become soft again, squeeze them in between your hands to remove all the excess water and crumble them into the tomato sauce. Add a cup of hot water.
Season with salt and cook on low flame for about ten minutes, stirring vigorously from time to time with a whisk to give the pappa al pomodoro its typical creamy texture.
Turn off the heat, add the torn basil leaves and pour over the soup the rest of the olive oil.
Set aside for at least an hour, allowing the flavors to mingle, then serve warm or at room temperature.