1 ½ 28ozcans whole peeled tomatoes (preferably a high-quality san marzano brand)
Kosher salt
Freshly ground black pepper
2small onions, diced
¼teaspoondried red pepper flakes
1quartchicken stock
2tablespoonsunsalted butter
1cupfresh basil
¼cuphalf and half
1tablespoonbalsamic vinegar
Grated parmesan or romano cheese, for serving
Instructions
Preheat the oven to 400 degrees Fahrenheit.
Take out a small baking dish and a large rimmed baking sheet.
Peel the extra layers of papery skin off of the garlic bulb until you can see the individual cloves, but leave the whole bulb intact. Cut the top off of the bulb, just enough to expose the top of each clove. Drizzle with olive oil, rub the oil all over the bulb, and wrap in aluminum foil. Place the wrapped head of garlic on the small baking dish & set aside.
Next, open the cans of tomatoes. Take the tomatoes out of the cans, one by one, squeezing each tomato gently and letting any extra juices drip back into the can. Cut each tomato in half, lengthwise, and place on the large rimmed baking sheet. Continue halving the tomatoes until you have filled your large baking sheet. Save any extra tomato juice and whole tomatoes for another use (perhaps a quick tomato sauce or shakshuka).
Drizzle the tomatoes with olive oil, and season liberally with kosher salt and freshly ground black pepper. Toss the tomatoes to coat well, and redistribute into neat rows.
Place the sheet of tomatoes and the small baking dish with the garlic in the oven and roast for about 40 minutes, until the tomatoes are golden and caramelized and the garlic is completely softened.
When the tomatoes and garlic are done, let cool for a few minutes, then use a spatula to scrape up the tomatoes and any caramelized bits from the baking sheet. Unwrap the garlic and squeeze each clove out of its skin. Set aside for later.
In a large soup pot, warm 2 tablespoons olive oil over medium heat until shimmering. Add the diced onions and red pepper flakes, and sauté, stirring occasionally, until the onions are softened and lightly browned.
Add the butter, tomatoes + their caramelized bits and any juices, roasted garlic, and chicken stock. Bring to a boil, then reduce the heat and simmer, uncovered, for 30 minutes.
Turn off the heat and stir in the fresh basil, half and half, and balsamic vinegar. Use an immersion blender to blend until smooth, or transfer to a blender and blend until smooth.
Ladle into bowls, sprinkle with cheese, and enjoy!