Preheat oven to 400°F Lightly grease a 1½-quart casserole, deep-dish pie pan, or 4 ramekins.
Place bread in a food processor and pulse to a coarse texture. Combine sugar, salt and pepper in a small bowl; mix well.
Arrange one-third of the tomato slices in the bottom of pan. Sprinkle one-third of the sugar mixture, one-third of the bread crumbs, and 1/3 cup Cheddar over tomatoes. Repeat with a second layer. For third layer, add remaining tomatoes, sugar mixture and bread crumbs. Dot with butter. Cover with foil.
Bake1 hour. Uncover and sprinkle remaining 1/3 cup Cheddar on top. Bake 5 minutes longer, or until cheese melts. Remove from oven and let stand 15 minutes before serving to allow the flavors to blend.