Step 1: Preheat oven to 400°. Place tomatoes in a greased 15x10x1-in. baking pan. Combine 1/4 cup oil and 4 cloves of garlic; drizzle over tomatoes. Toss to coat. Bake 15-20 minutes or until softened, stirring occasionally. Remove and discard skins.
Step 2: Meanwhile, in a Dutch oven, saute onion and 4 cloves of garlic in remaining oil until tender. Add tomatoes, water, salt and, if desired, pepper flakes. Bring to a boil. Reduce heat; cover and simmer 30 minutes or until flavors are blended. Cool slightly.
Step 3: In a blender, process soup in batches until smooth or just use an immersion blender. Return to pan. Stir in cream and heat through. Sprinkle with basil if desired.
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