Bring 4 cups of water and salt to a boil in a medium pot over high heat. Stirring constantly, add grits in a slow, steady stream. Lower heat to maintain a rapid simmer and cook, stirring, until water is absorbed and grits are smooth, about 5 minutes. Remove from heat and stir in butter and 1 ½ cups cheddar. Season to taste with salt and pepper.
Preheat broiler. Divide grits among six small, shallow, ovenproof bowls. Sprinkle evenly with bacon and top with a tomato slice. Sprinkle with remaining ½ cup cheese. Transfer bowls to a rimmed baking sheet and broil until cheese melts and is bubbling, about 1 minute. Serve immediately.
For the broiled tomatoes: Preheat broiler. Place sliced tomatoes on a baking sheet. Drizzle with olive oil and season with salt and pepper. Broil until softened, 2 to 3 minutes.
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