In a large skillet over medium heat, melt the butter. Reserve 10 tomatoes for garnish, then halve the rest. Add the halved tomatoes to the skillet. Cook until tomatoes are softened and just beginning to burst. Remove from heat and allow to cool slightly before transferring to a blender.

Blend the tomatoes until smooth. Transfer to a bowl and stir in the sambal oelek and horseradish and season with Kosher salt to taste. Set aside.

To assemble the skewers, skewer the shrimp head-side first with the shrimp kept in an upside down U-shape. Skewer the tomato and then skewer through the tail side of the shrimp. The tomato should be nestled into the curve of the shrimp. To finish, skewer the olive after the tail. Repeat the process with the remaining shrimp.

Serve the skewers with the buttery cocktail sauce and lemon wedges.