Preheat a grill for cooking over medium heat. Lightly oil the grill grates.
Spray a plate with cooking spray. Combine the ground beef, Worcestershire sauce, 1 tablespoon ketchup, 1 teaspoon salt and 1/4 teaspoon black pepper in a large bowl. Gently mix together, being careful not to overwork and toughen the meat. Divide the meat into 8 evenly sized balls. Thread the balls onto two 12-inch flat metal skewers, 4 balls per skewer; be sure to leave a little space between each ball. Place the skewers on the plate, and spray them with cooking spray. Keep refrigerated until ready to grill.
Place the 2 skewers on the grill and cover. Cook, flipping the skewers halfway through, until just cooked through, about 12 minutes. Remove from the grill and let cool slightly. Increase the heat of the grill to medium-high. Brush the meatballs all over with the remaining 2 tablespoons ketchup and cook until glazed.
Meanwhile, make 2 sandwiches consisting of 2 slices of American cheese between 2 slices of bread. Cut off the crusts, then cut each sandwich into 4 equal-sized squares.
Drizzle the iceberg lettuce with some oil and sprinkle with salt and pepper.
Build 4 skewers, each composed of: a cherry tomato, cheese sandwich square, meatball, a second cheese sandwich square, a second meatball, lettuce, 3 pickle slices, and a second cherry tomato.
Lay out a piece of aluminum foil large enough to hold the 4 skewers. Spray the foil with cooking spray and place on the grill. Arrange the skewers on the foil. Cover and cook 2 minutes, then carefully flip the skewers. Cover the grill again to melt and brown the other side of the skewers, about 1 more minute. Serve the skewers with ketchup and mustard.
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