In a large skillet over medium heat, cook the bacon about 10 minutes, turning occasionally, until crisp. Set on paper towels to drain.
Brush one side of each slice of bread with 1/2 teaspoon of olive oil. Flip the bread over, oiled sides down, then spread each slice with a tablespoon of barbeque sauce. Place a slice of cheddar on four of the pieces of bread, then set two slices of bacon on top of the cheddar. Finish with one more slice of cheddar, and top with the bread, oiled side facing up.
Heat a large skillet over medium heat. Set two of the sandwiches in the skillet, and reduce heat to medium-low. Cook 6-8 minutes, flipping halfway through the cooking time, until golden. Repeat with the remaining sandwiches, and enjoy!