Pimento Grilled Cheese Recipe

Combine 3/4 cup balsamic vinegar and 1 tbsp brown sugar (or honey) in a small saucepan. Bring to a gentle simmer over medium heat, then reduce heat to low and simmer until syrupy and reduced by about half, 8–12 minutes. Stir occasionally to prevent burning.

Remove from heat and let cool slightly; the reduction will thicken as it cools. Season with 1/4 tsp kosher salt and a pinch of freshly ground black pepper. If desired, whisk in 1 tsp olive oil for a glossier finish. Keep warm at room temperature.

Clean mushrooms by wiping with a damp cloth or gently rinsing and patting dry; slice larger ones in half or thickly if necessary so pieces are about 1/4–1/2 inch thick.

Toss mushrooms with 1 tbsp olive oil, 1 tsp minced garlic, 1/4 tsp salt and 1/8 tsp black pepper in a bowl until evenly coated.

Heat a medium nonstick or cast-iron skillet over medium-high heat until hot. Add the mushrooms in a single layer and cook without moving for 2–3 minutes to develop color, then stir or flip and continue cooking another 2–3 minutes until golden and tender. Remove from heat and set aside.

Slice the green tomatoes into 1/3–1/2-inch rounds; you should get 8–10 slices from 2 medium tomatoes. Pat slices dry with paper towels.

Set up a dredging station: shallow bowl with 3 tbsp flour mixed with 3 tbsp cornmeal, 1 tsp salt and 1/2 tsp black pepper; second bowl with 1 beaten egg mixed with 2 tbsp milk.

Heat 3 tbsp vegetable oil in a 10-inch skillet over medium heat until shimmering but not smoking. Dip each tomato slice first in flour-cornmeal mixture (shake off excess), then in egg wash, then again in the flour-cornmeal to coat.

Fry tomatoes in batches for 2–3 minutes per side, until golden brown and crisp. Transfer to a paper-towel-lined plate and season lightly with a pinch of salt. Keep warm in a low oven (200°F/95°C) while assembling sandwiches.

Grate the cheddar if not pre-grated. Spread about 3 tablespoons of pimiento cheese evenly on one side of 4 slices of bread (this will be the interior spread).

On top of the pimiento cheese layer, divide the grated cheddar evenly among the 4 sandwiches (about 1/4 cup per sandwich).

Top the cheese with a layer of baby spinach (about 1/2 cup per sandwich), then distribute the grilled mushrooms evenly over the spinach, and place 2 fried green tomato slices on each sandwich (or enough to cover).

Close sandwiches with remaining bread slices. Butter the exterior sides of each sandwich evenly with softened butter (about 1 tablespoon per side).

Heat a large skillet or griddle over medium-low to medium heat. Place sandwiches in the pan and cook 3–4 minutes per side, pressing gently with a spatula, until bread is golden brown and cheese is melted. If the bread is browning too quickly before cheese melts, lower the heat and cover the pan with a lid for 1–2 minutes to allow the cheese to melt through.

Remove sandwiches from the pan and let rest 1 minute, then slice each sandwich in half on the diagonal.

Arrange sandwiches on plates. Drizzle balsamic reduction over the top of each sandwich and around the plate (about 1–2 teaspoons per sandwich). Finish with a light grind of black pepper if desired.