For the Black Pepper Bacon: Preheat the oven to 400˚F. Line a baking sheet with aluminum foil and top with a baking rack. Spray lightly with cooking spray.
Add bacon in an even layer. Sprinkle it evenly with black pepper. Bake until crisp, about 10 to 15 minutes.
For the Tomato Slices: Thickly slice the tomatoes. Place on a serving plate, drizzle with olive oil. Sprinkle it with salt and pepper. Place in the refrigerator until ready to serve.
For the Caramelized Onions: In a skillet over medium heat, melt butter with oil. Once hot, add sliced onion. Season with salt and pepper. Cook down slowly, stirring occasionally, until well caramelized, about 15 to 20 minutes.
For the Grilled Pineapple: Grill pineapple on each side for about 4 to 5 minutes, until softened.
For the Burgers: Preheat the grill to medium high heat. Lightly oil the grill grates.
In a large bowl, combine ground beef and Head Country Bar-B-Q seasoning. Use your hands or a big spoon to bring the mixture together. Be sure to only work the mixture until just combined. If you overwork the combination it will be too tough.
Shape the beef into 6 patties.
Add the burgers to the grill. Cook for 4 minutes per side for medium-rare. For rare, cook for 3 minutes per side. For medium to medium well, cook for 5 to 6 minutes per side. If you would like to use cheese, add a cheese slice to each patty during the last minute of cooking.
For the Burger Bar: While the burgers are cooking, assemble the burger bar with the gourmet toppings and classic toppings.
Remove burgers to a plate and serve.