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Spread the butter onto the bottom and sides of a 7- to 8-inch cast-iron skillet or two individual 10- to 12-ounce cast-iron skillets or casseroles. In a medium bowl, stir together flour, ginger, baking soda, cinnamon, cloves and salt; set aside.
In another medium bowl, beat shortening with an electric mixer on low speed for 30 seconds. Add sugar. Beat until combined, scraping the sides of the bowl often. Add egg and molasses, beating until combined. Beat in as much of the flour mixture as you can with the mixer. Stir in any remaining flour mixture with a wooden spoon. Spread to an even thickness in the prepared skillet(s).
Arrange medium-hot coals around the edges of a charcoal grill, leaving the center of the grill with no coals. Test for medium heat above the center of the grill. Place skillet(s) on the grill rack over the center of the grill (not over the coals). Cover and grill until edges of cookie are set. Allow 15 to 18 minutes for the large skillet or 10 to 12 minutes for the small skillets. For the last 5 to 10 minutes of grilling, add pineapple slices to grill, placing them directly over the coals; cover and grill until pineapple is golden brown, turning once halfway through grilling. (For a gas grill, preheat grill. Adjust for indirect cooking. Place skillet(s) on unheated side of grill and later place pineapple over heat. Grill as above.)
Cool slightly (center will fall slightly). If desired, drizzle with caramel topping. Serve with grilled pineapple and ice cream.