> 3 (28 oz) cans whole peeled tomatoes
> 3 tbsp olive oil, divided
> 2 whole bulbs garlic
> 1 tsp sugar
> 4 tbsp heavy cream
Preheat oven to 400°F. Line a large rimmed baking sheet with parchment. Drain the tomatoes, reserving tomato juice from cans. Spread canned whole tomatoes on baking sheet. Drizzle with 2 tbsp oil. Season with salt and pepper.
Remove and discard any loose papery skin from the garlic bulbs, but leave cloves unpeeled. Using a sharp knife, cut ¼ inch from top of bulbs to expose garlic cloves. Place bulbs in the center of a double layer of foil. Drizzle with remaining 1 tbsp oil, wrap up tightly, and place on baking sheet. Roast 45–50 min., until tomatoes are slightly caramelized on bottoms.
Unwrap garlic and let cool. When cool to the touch, squeeze each garlic clove out of its peel into a large pot. To pot, carefully add roasted tomatoes. Add reserved tomato juice, sugar, and 2 tbsp cream, then season with salt and pepper. Using an immersion blender, purée soup until smooth. (Or use a blender to purée the soup in batches.) Heat pot briefly on medium-high until soup is warm. Ladle into bowls or mugs and drizzle with remaining 2 tbsp cream.