Parmesan Bread Pudding with Broccoli Rabe and Pancetta
['1 tablespoon olive oil', '2 garlic cloves, thinly sliced', '1/2 teaspoon crushed red pepper flakes', '1 medium bunch broccoli rabe (rapini), trimmed, cut into 1/2" pieces', '2 teaspoons kosher salt plus more', '1/2 teaspoon freshly ground black pepper plus more', '6 large eggs', '1 1/2 cups whole milk', '1/2 pound country-style white bread, cut into 1" pieces (about 8 cups)', '1/2 cup plus 2 tablespoons finely grated Parmesan', '6 thin slices pancetta (Italian bacon)']
Preheat oven to 350°F. Heat oil in a large skillet over medium heat. Add garlic and red pepper flakes. Stir until garlic is softened, about 30 seconds. Add broccoli rabe; season with salt and pepper. Cook, tossing, until wilted, about 2 minutes; let cool slightly.
Meanwhile, whisk eggs, milk, 2 teaspoons salt, and 1/2 teaspoon pepper in a large bowl to blend. Add broccoli rabe mixture, bread, and 1/2 cup Parmesan; toss to combine. Transfer to a 1 1/2-quart baking dish. Top with pancetta and remaining 2 tablespoons Parmesan.
Bake pudding until puffed, browned in spots, and set in the center, 45-55 minutes.
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