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Cooks' note: Bread pudding is best the day it is made but can be made 1 day ahead and chilled (covered once cool). Reheat, covered with foil, in a 350°F oven.
3 pounds plum tomatoes such as Roma, halved lengthwise
1 1/2 teaspoon Herbes de Provence
1/2 cup extra-virgin olive oil, divided
1 head garlic, left whole
10 cups cubed (1-inch) country-style Italian bread (1 pound)
2 cups whole milk
1 cup heavy cream
8 large eggs
2 cups coarsely grated chilled Italian Fontina (9 ounces)
1/2 cup grated Parmigiano-Reggiano
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