Preheat the oven to 400 degrees F. 

On a large sheet pan, drizzle some olive oil. Prepare the tomatoes by slicing the tops  (stem side) off and place on the pan sliced side down. Then score the opposite ends with an “x,” just slicing the skin. As the tomatoes roast, the heat will cause the skins to start to peel away from the flesh and will make it a whole lot easier to remove them after roasting. You can set aside the skins on a sheet of parchment paper to make tomato powder (instructions here) if you really want to reduce some waste. Peel the onion and slice it into rings and place on the same pan. Add the garlic. You don’t have to peel it yet, you can do that after the roasting and it will make them easier to peel. Place 3 of the basil leaves and one sprig of oregano under the tomatoes. Drizzle olive oil on top of tomatoes, onions, and garlic.

Roast tomatoes, garlic, and onion for 40-45 minutes. 

Allow the roasted vegetables to cool. Once they are cool enough to touch, peel the skins off of the tomatoes and remove the skins off of the garlic cloves. 

Separate the oregano leaves from the stems. Keep the oregano that was roasted with the roasted vegetables, but set aside the remaining oregano for the next step.

In a large pot, heat about a tablespoon of olive oil on medium high heat. Once the oil is warm, add the oregano and allow it to heat through for a minute. Don’t burn it. Then add the tomatoes, onion, garlic, basil, oregano, and bay leaf. 

Start squishing the tomatoes with a spoon while in the pot to get the juices going. Allow the ingredients to cook together for 2-3 minutes, stirring to not allow the ingredients to burn.

Now add the chicken broth. Simmer for 30 minutes (or longer if you want a thicker soup). 

Remove the bay leaf. Use an immersion blender to break up the ingredients until the soup is your desired smoothness. If you don’t have an immersion blender, you can pour the soup into a regular blender in batches to smooth it. 

Remove from heat and if desired, add the heavy cream.