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Melt butter in a large saucepan over medium-low heat. Add onion and garlic, and cook until onion is translucent, about 6 minutes.
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Add wine, and cook until most liquid has evaporated, about 1 minute. Add tomatoes, stock, and oregano, and bring to a boil. Reduce heat, and simmer gently until thickened, about 45 minutes.
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Using a slotted spoon, remove herbs. Puree soup in small batches until smooth. Return to pan, and slowly pour in half-and-half, stirring constantly. Season with salt and pepper.
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Meanwhile, make the bugs: Use a toothpick to pierce each Kalamata olive 4 times (all the way through to other side). Insert a rosemary leaf into each hole to make eight legs. Insert two pieces of chive into the small hole at the end of the olive to make antennae.
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Make the eyeballs: Using a small melon baller, scoop out a hole from each bocconcini. Have each pimiento-stuffed olive crosswise. Place a half, cut side out, in the hole in each bocconcini to make eyeballs.
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Ladle hot soup into shallow bowls. Float 4 or 5 eyeballs in soup, and place a bug on rim of each bowl.