Gourmet Grilled Cheese with Roasted Tomatoes

Why This Works

Roasting the tomatoes first concentrates their flavor and drives off moisture, so the sandwich never goes soggy. Two cheddars do different jobs: a sharp aged cheddar for bite, a smoked cheddar for creamy depth.

Ingredients

Sourdough bread (4 thick slices)
Aged vintage cheddar, such as 1833 Vintage Reserve (2-3 oz, sliced or shredded)
Smoked cheddar, such as Ashley Cheese Estate Smoked Seaside (2-3 oz, sliced or shredded)
Heirloom tomatoes (1-2 medium, sliced ¼" thick)
Butter (2-3 Tbsp, for grilling)
Olive oil (a drizzle, for the tomatoes)
Salt and pepper (for the tomatoes)

Method

Roast the tomatoes (10 minutes). Preheat the oven to 425°F. Slice the tomatoes into ¼-inch rounds, arrange on a parchment-lined baking sheet, drizzle with olive oil, and season with salt and pepper. Roast 8-10 minutes, until slightly softened and the edges begin to caramelize.
Assemble. Lay out the bread. On 2 slices, layer the aged cheddar, then the roasted tomato slices, then the smoked cheddar. Close with the remaining slices.
Grill (8-10 minutes). Heat a large skillet or griddle over medium heat. Butter the outside of each sandwich generously, and cook 4-5 minutes per side, pressing gently with a spatula for even browning, until the bread is golden and crispy and the cheese is fully melted.

Notes

Cheese pairing: the sharp aged cheddar complements the smoky, creamy one — any good aged + smoked cheddar combination works.
Bread thickness: thick-cut sourdough gives a sturdy base and great texture contrast.
Temperature control: medium heat prevents burning while letting the cheese melt fully.
Make-ahead: roast the tomatoes in advance; assemble and grill when ready.
Variations: add fresh basil leaves or arugula.
Perfect pairing: a bowl of homemade tomato soup.