For bacon: Place rack in center of oven and preheat to 400°F.
Line large rimmed baking sheet with foil. Arrange bacon slices in single layer on flat ovenproof rack set on prepared baking sheet. Bake bacon 10-15 minutes, until crispy. Place bacon between two paper towels and pat dry. Halve each slice and set aside.
For sandwich: Preheat cast-iron skillet to medium low; add 1 tablespoon butter and melt. In small bowl, gently smash raspberries and stir with jam and chipotle chile, mashing together with the back of spoon. Mixture should remain fairly chunky.
For each sandwich, layer 1 slice of bread with 1/4 of the cheddar, 1/4 of the berries, four half-slices of bacon, an additional 1/4 of the berries, then an additional 1/4 of the cheese. Carefully set the loaded bread slice down in the hot skillet. Place another bread slice on sandwich, then spread with half of remaining butter. Grill slowly until bread is golden and cheese melts, flipping once, about 4 to 5 minutes per side. Cover the skillet, if desired, to aid melting. Repeat with second sandwich. Slice and serve immediately.
- 4 slices thick-cut bacon
- 2 tablespoons unsalted butter, softened, divided
- 6 ounces fresh raspberries
- 2 tablespoons raspberry or strawberry jam
- 1/4 teaspoon dried chipotle chile
- 4 thick slices sourdough bread
- 6 ounces Wisconsin Aged White Cheddar cheese, sliced