Preheat oven to 400° F. Slice the tomatoes in half and place them on a baking sheet along with the garlic cloves (leave peel on).
3 lb ripe tomatoes**, 8 garlic cloves
Drizzle olive oil over the top. Sprinkle fine sea salt, ground black pepper, and paprika over the tomatoes and garlic, and then toss the tomatoes and garlic with your hands so that they are evenly coated in spices and olive oil. Place the baking sheet in the oven to roast for 40-45 minutes. The tomatoes should be slightly charred.
¼ cup olive oil, 1 teaspoon fine sea salt, ¼ teaspoon ground black pepper, 1 teaspoon paprika
While the tomatoes and garlic are roasting, dice the medium yellow onion and add it to a large pot. Saute the onions with the salted butter until they are soft and translucent. You'll want them to cook as long as possible without burning them.
1 medium yellow onion, 3 tablespoon salted butter
Let the tomatoes and garlic cool for 10 minutes and then set aside the garlic cloves. Add the tomatoes to a large blender and make sure to scrape all of the extra juices burned bits from the baking sheet and add them to the blender--these have a lot of flavor that you don't want to miss. Take each garlic clove, and squeeze out the softened inside into the blender, then discard the peel.
Also add the sauteed onions, vegetable broth, and handful of fresh basil (any hard stems removed) to the large blender. Blend until smooth.
1 ½ cup vegetable broth***, handful of fresh basil****
Pour the contents of the blender back into the pot that the onions were cooked in. Add red pepper flakes, dried oregano, cane sugar, and salt. Stir. Bring it to a boil, then cover with a lid and turn the heat down to low, letting it all simmer for about 10 minutes.
¼ teaspoon red pepper flakes, ½ teaspoon dried oregano, 1 teaspoon cane sugar*****, ½ teaspoon fine sea salt (or more, add to taste)
Leave the heat on low, and stir in the heavy cream. (Add more if wanted.) Keep warm until serving.
¼ cup heavy cream