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Heat 2 tablespoons oil in a large ovenproof skillet over medium heat. Add onion, bell pepper, mushrooms, garlic and 1/4 teaspoon each salt and pepper; cook, stirring occasionally, until the mushroom liquid has evaporated, 10 to 12 minutes. Whisk Madeira (or sherry) and tomato paste in a small bowl; add to the skillet. Cook, stirring, until the liquid turns syrupy and is almost absorbed, about 2 minutes.
Add wild rice, tomatoes, broth, water, saffron and 1/4 teaspoon each salt and pepper. Bring to a boil over medium-high heat. Reduce heat, cover and simmer for 40 minutes. Uncover and simmer until the rice is tender and most of the grains are “popped,” 20 to 30 minutes more.
Meanwhile, preheat oven to 400°F.
Toss Brussels sprouts and sweet potato with the remaining 2 tablespoons oil and a pinch each of salt and pepper. Spread the vegetables in a single layer on a rimmed baking sheet. Roast, stirring once halfway through, until tender and browned in spots, 18 to 20 minutes.
Reduce oven temperature to 350°.
When the rice is done, arrange the roasted vegetables decoratively on top of it. Transfer the skillet to the oven to heat through before serving, 5 to 10 minutes.