Slow-roasted tomato bisque with arugula grilled cheese

I love rainy Saturdays, especially in the fall.  It's not officially fall yet, but today is Saturday and a cool 55 degrees and rainy.  Mizzou football tonight.  Crisp breeze.  Love it.  Let's just call it fall.

Any sane person living in the Midwest like me would agree that this is a soup kind of day.  My trip to the farmer's market this morning was inspired by the weather, and I ended up with some heirloom tomatoes (coincidence?)... perfect for soup-making.
It was meant to be. 

Slow-roasted tomato bisque with arugula grilled cheese
Serves 4

For the soup:
2 pounds tomatoes (any kind is ok!)
8 cloves garlic, 4 unpeeled and 4 peeled and chopped
2 cups vegetable broth
1 medium leek
2 shallots
3 Tbsp flour
2 tsp sugar
Olive oil
6 large basil leaves
Black pepper
1/4 cup rice

Preheat oven to 250.  Slice all but 3 tomatoes in half lengthwise and arrange the sliced tomatoes on a baking sheet.  Toss the 4 unpeeled garlic cloves onto the sheet and drizzle everything with olive oil.  Bake for 90 minutes or until the tomatoes are soft and well-roasted.
Meanwhile, you can get your other ingredients ready.  Prepare your veggie broth (if you're making it yourself) by simmering some carrots, celery, and onion in a pot with 3+ cups of water.
Chop the 3 non-roasting tomatoes and set aside.  Finely chop the 4 remaining garlic cloves, leek, and shallots.
When the tomatoes are finished, transfer them to the bowl with the raw diced tomatoes.  Remove the roasted garlic cloves, peel and chop them, and add them to your pile of tomatoes.
WIth a wooden spoon, carefully scrape the caramelized juices of the tomatoes from the baking sheet, using the leftover olive oil on the sheet to help soften it up.  Transfer all of the juices and oil to a large pot, add the leek, shallots, and raw garlic, and cook over medium heat until softened, about 7 minutes (add more olive oil if you need it).  Add the flour and stir until incorporated.  The mixture should thicken quite a bit.
Add your tomatoes and roasted garlic pile, rice, sugar, basil leaves, parsley, and any other spices you want to use.  Let this mixture cook for 15-20 minutes or until the rice is cooked.  It should look slightly unattractive:
Using a regular blender (you may have to do 2 batches) or an immersion blender (get one!), blend up the mixture until it is nice and smooth.  At this point, if you want, you could strain this through a fine mesh strainer or use a food mill to remove any leftover seeds and skins for an extra smooth soup.  I added some Parmigiano Reggiano to mine.

For the arugula grilled cheese:
2 slices bread
2 slices fresh mozzarella
3-4 arugula leaves
2 thin slices butter

Easy.  On one slice of bread, but 2 slices of mozzarella and top with the arugula.  Add slice of bread #2.
Place on warmed pan on stove with a sliver of butter on top and on bottom.  Let one side brown, then flip.  Done.

This meal is absolutely best eaten by dipping the sandwich in the soup.  But I won't judge if you don't.  But maybe I will a little.  It's just the right thing to do.

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