Cheesy Sausage and Sage Stuffing
['2 tablespoons unsalted butter, plus more', '1 medium boule sourdough, cut into 1-inch pieces (9–10 cups), dried out overnight', '2 tablespoons olive oil', '1 pound sweet or spicy Italian sausage, casings removed', '2 large onions, finely chopped', '3 celery stalks, chopped', '1/4 cup finely chopped sage', 'Kosher salt, freshly ground pepper', '1 cup dry white wine', '2 large eggs, beaten to blend', '1 cup low-sodium chicken broth', '2 cups half-and-half', '1 pound aged cheddar', 'grated (about 5 cups)', 'divided']
Preheat oven to 300°F. Butter a shallow 13x9" baking dish and a large piece of foil. Place 9 cups bread in a large bowl.
Heat oil in a large skillet over medium-high. Cook sausage, stirring occasionally and breaking into small pieces with a wooden spoon, until browned and cooked through, 7–10 minutes. Transfer to bowl with bread.
Place onions, celery, sage, and 2 Tbsp. butter in same skillet; season with salt and pepper. Cook, stirring often, until onions are golden brown and soft, 10–12 minutes. Add wine and cook, stirring occasionally, until almost completely evaporated, about 5 minutes; scrape into bowl with bread and sausage.
Whisk eggs and broth in a medium bowl until smooth, then pour over bread mixture. Pour in half-and-half and add 3 cups cheese; toss to combine. Season with salt and pepper. Transfer to prepared baking dish and cover with foil, buttered side down. Bake until a paring knife inserted into the center comes out hot, 40–50 minutes .
Heat broiler. Uncover stuffing and top with remaining cheese. Broil until top is golden and bubbling, about 4 minutes. Let sit at least 10 minutes and up to 30 before serving.
Stuffing can be assembled 1 day ahead; cover with foil and chill. Stuffing can be baked (but not broiled) 3 hours ahead. Store tightly wrapped at room temperature until ready to broil.
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