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Preheat oven to 350F.
In a large bowl, mix together ground beef, bread crumbs, barbecue sauce, eggs, salt and pepper. Pack into a loaf pan.
Bake for 1 hour 5 minutes. Invert on a platter and cut into slices. Add a slice of pineapple between each slice of meatloaf. Insert a cherry inside each slice of pineapple.
To make the sauce, add reserved pineapple syrup, water and cornstarch to a pot and bring to a boil. Stir constantly. Turn down heat to medium and continue to cook until thickened. Stir in barbecue sauce.
Pour sauce over meatloaf and serve.