This classic combination works best on raisin bread. Sobocinski suggests serving the sandwich with St. Francis Cabernet, highlighting the wine's hints of black currant fruit, oak, vanilla, and tobacco.
Preheat oven to 400 degrees.
Lay the bacon out onto a sheet pan lined with parchment paper. Cook in the oven for 12-17 minutes or until nicely browned and crisp.
Remove bacon from sheet pan onto a dish lined with a paper towel and allow to drain and cool.
Butter one side of each of the slices of raisin bread equally with the 2 tablespoons of butter.
Assemble the sandwiches by placing a quarter of the shredded Cheddar on the unbuttered side of one slice of bread, then 2 slices of apple, a pinch of cayenne (or more if you like), then 3 slices of crisp bacon, then more shredded Cheddar, all topped off with raisin bread, butted side facing out.
In a large sauté pan, cook the sandwiches on one side until golden brown, flip, and finish cooking in the preheated oven until nicely melted through. Allow sandwiches to rest for 3 minutes before cutting or eating.