Ingredients

  • 8 large ripe tomatoes (about 3 pounds)
  • 1 cup tomato juice (optional; see Note)
  • 3 garlic cloves, very finely chopped
  • Kosher salt and freshly ground pepper
  • 1/4 cup plus 2 tablespoons extra-virgin olive oil
  • 1 large baguette (12 ounces), sliced on the diagonal 3/4 inch thick
  • 5 tablespoons minced flat-leaf parsley
  • 5 tablespoons very finely chopped basil

Method

  • Bring a large saucepan of water to a boil and fill a large bowl with ice water.
  • Using a sharp knife, make a shallow X in the bottom of each tomato.
  • Plunge the tomatoes into the boiling water for 10 seconds, then immediately transfer them to the ice water.
  • Peel and core the tomatoes and halve them horizontally.
  • Set a strainer over a medium bowl and scoop the seeds and pulp from the tomatoes into it.
  • Press the pulp to extract as much of the juice as possible; there should be 1 cup.
  • If not, add enough of the tomato juice to make 1 cup.
  • Arrange the tomatoes, cut side up, on a large plate, sprinkle with the garlic and season with salt and pepper.
  • Drizzle with 2 tablespoons of the olive oil and let stand for 30 minutes.
  • Add any juices that accumulate on the plate to the strained tomato juice.
  • Preheat a cast-iron grill pan or preheat the broiler.
  • Brush the baguette slices on both sides with the remaining 1/4 cup of olive oil and grill until golden, about 1 minute per side.
  • Transfer the toasts to a large plate.
  • Add the tomatoes, cut side down, to the grill and cook just until lightly charred, about 1 minute.
  • Return the tomatoes to the plate and flatten slightly with a spatula.
  • Preheat the oven to 350.
  • Lightly oil a shallow 8-by-11-inch baking dish and arrange half of the tomatoes on the bottom.
  • Sprinkle the tomatoes with 2 tablespoons each of parsley and basil and season with salt and pepper.
  • Top with half of the toasts; repeat with the remaining tomatoes, 2 tablespoons each of parsley and basil and the remaining toasts.
  • Pour the tomato juice over the toasts.
  • Lightly oil a sheet of parchment paper and place it directly on the toasts.
  • Cover the bread pudding with foil, pressing slightly to compact it.
  • Bake the bread pudding in the center of the oven for about 45 minutes, or until the liquid is absorbed and the tomatoes are very soft.
  • Remove the foil and parchment and bake about 10 minutes longer, or until crisp.
  • Let the tomato bread pudding stand for 15 minutes, then sprinkle with the remaining 1 tablespoon each of parsley and basil and serve.