Drizzle half of the olive oil onto the sheet tray. Then, add the cherry tomatoes, onion, and garlic. Drizzle the rest of the olive oil over the top, and season generously with salt and pepper.
⅓ cup olive oil, 3 twelve ounce packages cherry tomatoes, 1 small yellow onion, 1 garlic clove, kosher salt and black pepper
Bake for 35-45 minutes or until the tomatoes have burst and begun to caramelize around the edges.
Remove from the oven, and allow to cool for five minutes.
Add the tomatoes, onion, and garlic, as well as any juices from the sheet tray, to a high-powered blender. Blend on medium-high speed for one minute, or until fully pureed. Taste and season with additional salt, pepper, and sugar, if needed.
sugar
While the tomatoes are blending, bring two cups of water to a boil.
If more liquid is needed to thin the consistency of the soup, add half of the hot water to the sheet tray. Scrape up any browned bits with a wooden spoon or spatula. Carefully transfer the water mixture to the blender, and pulse to combine. Add more water as needed, working in 1/4 cup increments, until the desired consistency is achieved.
Add the heavy cream, and blend again for 20 seconds. If the mixture is too thick, add ¼ cup of water incrementally, or until the desired consistency is achieved. Season to taste, adding sugar as needed.
¼ cup heavy cream
For the Grilled Cheese
On one side of each piece of bread, spread the mayonnaise and one tablespoon of butter over the surface, all the way to the edges. Sprinkle 1/4 cup of Parmesan evenly over the mayonnaise, and lightly press into the surface of the bread.
2 slice sourdough bread, 4 tablespoon mayonnaise, 2 tablespoon butter, ½ cup Parmesan cheese
Flip each piece over, and add the cheddar, Gouda, and Fontina cheese to one piece of bread. Top with the second piece and set aside.
In a medium nonstick skillet over medium heat, add one tablespoon of butter. Once the butter is lightly sizzling, add the grilled cheese. Cook for three to four minutes, or until one side is deeply golden brown. Then, flip, and cook for another three to four minutes.
In the last one to two minutes of cooking, cover the skillet with a lid to allow the grilled cheese to lightly steam and completely melt the cheese.
Remove the grilled cheese from the pan, and turn the heat to low. Add the remaining Parmesan cheese directly onto the skillet.
Add the grilled cheese back to the skillet, directly on top of the Parmesan. Cook for one to two minutes or until the Parmesan is crispy and crunchy on the bottom.
Transfer to a cutting board and let the grilled cheese cool for two to three minutes. Once it is cool enough to handle, slice the grilled cheese in half and serve it with tomato soup topped with fresh parsley, if desired.
fresh parsley
Video
Notes
Storage: I don't recommend storing leftover grilled cheese sandwiches. However, leftover soup will keep fresh in an airtight container in the refrigerator for up to three days, or in the freezer for up to four months.