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Preheat the oven to 300°F.
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Line a rimmed baking sheet or roasting pan with foil. Set a baking rack on top that fits. Grease with nonstick spray.
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In a medium bowl, mix the brown sugar, Italian seasoning, salt, paprika, garlic powder, onion powder, black pepper, and red pepper flakes.
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Place the chicken on a large plate and drizzle with oil. Massage the oil all over the chicken and underneath the skin.
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Sprinkle the spice mixture all over the chicken and rub some underneath the skin.
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Place the chicken on the prepared rack, breast side up. Tie the legs with baking twine and tuck the wings under.
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Bake for 2 1/2 hours, or until the thickest part of the breast registers 165°F–175°F on an instant-read thermometer.
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Rest 15 minutes before carving.