Make the Tomato Soup:

1. Heat olive oil in a Dutch oven over medium-high heat. Add onion and ½ tsp salt, cooking for 7-9 minutes until translucent.
2. Stir in tomato paste and garlic, sautéing for 2 minutes until fragrant.
3. Add crushed tomatoes, whole peeled tomatoes, broth, Worcestershire sauce, and brown sugar. Stir well and bring to a boil.
4. Reduce heat to low and let simmer for 5 minutes.
5. Carefully transfer soup to a high-speed blender and blend until completely smooth.
6. Return to Dutch oven and keep warm on low heat while preparing grilled cheese.

Make the Grilled Cheese:

1. Place two slices of American cheese and one slice of gouda between two slices of sourdough bread.
2. Spread butter on one side of the sandwich.
3. Heat a large skillet over medium heat and place the sandwich butter-side-down. Cook for 3-4 minutes.
4. Spread mayonnaise on the top slice while the bottom side cooks.
5. Flip and cook for another 2-4 minutes, covering the pan to ensure the cheese melts.
6. Remove from heat, slice in half, and serve with warm tomato soup.