Marcelle Bienvenu’s Fantastic Tomato Bread Pudding

2 T. butter
3 large tomatoes, cut into wedges
2 t. salt, divided
1 t. black pepper divided
8 T. olive oil, divided
10 c. cubed French or Italian bread
2 c. whole milk
8 eggs
1 c. shredded fontina cheese
1 c. shredded mozzarella cheese
½ c. grated Parmesan cheese
2 T. chopped fresh basil
2 T. chopped fresh oregano

1. Preheat oven 400.
2. Coat 3 qt. shallow baking dish with butter. Line a rimmed baking sheet with parchment paper.
3. In large bowl, toss tomato with 1 t. salt, ½ t. pepper and 2 T. olive oil.
4. Arrange tomato in one layer on prepared baking sheet; roast until lightly browned, about 30 minutes. Remove from oven and let cool.
5. Toss cubed bread with remaining olive oil and spread on baking sheet and bake until golden brown and let cool.
6. Reduce oven to 350.
7. In large bowl, whisk together milk, cream and eggs. Season with remaining salt and pepper.
8. Stir in cheeses, basil and oregano.
9. Transfer bread cubes to prepared baking dish and pour egg mixture over bread.
10. Add tomatoes, pushing them down into bread and custard.
11. Bake until firm to the touch and bread is golden brown, 45-60 minutes.
12. Serve warm.