Heat oven to 425ºF.
Cut each tomato in half lengthwise. Arrange in a shallow baking dish, cut-side down, with the garlic and crushed red pepper. Bake about 40 minutes or until the garlic is soft and the tomato skins pucker and brown.
Remove from oven. Peel off the tomato skins and discard. Using the back of a fork, smash the garlic and break up the tomatoes in the baking pan. Blend in the olives, basil, vinegar, and salt.
Serve over 1 pound of cooked pasta or with grilled fish or chicken.