Preheat oven to 350ºF (177ºC). Spray a 9x5-inch loaf pan with nonstick cooking spray. Line a large-rimmed baking sheet with foil or parchment paper and spray with nonstick cooking spray; set aside.
Heat oil (2 tablespoons) to a 12-inch skillet, over medium heat and sauté, stirring frequently, onion (1 cup), green bell pepper (1/2 cup), and garlic (4 cloves) until tender, about 5 minutes. Remove from heat and cool.
In a large mixing bowl, Add bread crumbs (1 cup), milk (1/2 cup), drained pimientos (1 jar), bbq sauce (1/4 cup), Worcestershire sauce (1 tablespoon), eggs (2), ground beef and pork (1 pound each), smoked paprika (2 teaspoons), Cajun seasoning (1 1/4 teaspoons), salt (1/2 teaspoon), black pepper (1/4 teaspoon), and cooled sautéd vegetable mixture. Gently mix with your hands to evenly combine. Do not overmix!
Evenly press the meatloaf mixture into the prepared pan. Invert the pan onto the foil-lined baking sheet.
Pour half the remaining 3/4 cup BBQ sauce over the meatloaf. Brush the sauce over top and sides in an even layer. Bake in preheated oven for 40 minutes.
Remove the meatloaf from the oven. Increase oven temperature to 400ºF (204ºC). Brush the remainder of the sauce over top and sides in an even layer.
Return the meatloaf to the oven and cook until meatloaf registers 160ºF (71ºC), about 15-20 minutes. Allow meatloaf to cool for 10 minutes then serve.