Prepare the Pork: Pat the pork tenderloins dry with paper towels to help the seasonings adhere better and promote even browning. Rub with olive oil, then season all sides with salt, black pepper, smoked paprika, garlic powder, and onion powder. Let the pork sit at room temperature for about 20 minutes while you prepare the glaze.
Make the Bourbon BBQ Glaze: In a small saucepan, combine the barbecue sauce, bourbon, brown sugar, Dijon mustard, Worcestershire sauce, minced garlic, apple cider vinegar, and smoked paprika. Stir well and place over medium heat.
Simmer and Thicken the Glaze: Bring the mixture to a gentle simmer and cook for 8 to 10 minutes, stirring occasionally. As the glaze cooks, it will thicken slightly and develop deeper sweet-smoky flavors. Remove from the heat and set aside.
Preheat the Grill: Preheat your grill to medium-high heat, about 400°F (204°C). Clean the grates thoroughly and lightly oil them to help prevent sticking and create better grill marks.
Grill the Pork Tenderloins: Place the pork directly on the grill and cook for 18 to 22 minutes, turning every few minutes to ensure even cooking. The exterior should begin developing a lightly charred crust while remaining juicy inside.
Brush with the Bourbon Glaze: During the final 8 to 10 minutes of cooking, begin brushing the pork generously with the glaze. Apply several thin layers, turning and glazing every few minutes to build a beautiful sticky coating and maximize caramelization.
Check for Doneness: Use an instant-read thermometer to monitor the internal temperature. Cook until the thickest part of the pork reaches 145°F (63°C). This ensures a tender, juicy result without drying out the meat.
Rest the Pork: Transfer the pork tenderloins to a cutting board and loosely tent with foil. Allow them to rest for 5 to 10 minutes so the juices can redistribute throughout the meat.
Slice and Serve: Slice the pork into thick medallions against the grain for maximum tenderness. Arrange on a serving platter and drizzle with additional bourbon barbecue glaze.
Garnish and Enjoy: Finish with chopped parsley, sliced green onions, or one final brush of glaze for extra flavor and visual appeal. Serve immediately while warm and enjoy every sweet, smoky, caramelized bite.