Tomato…Tomahto…Soup, and Grilled Cheese (Wisconsin Style)

So, it was a rainy November sunday. The day started out with a tornado watch, then progressively got cold, windy and miserable. A typical Wisconsin pre-winter day. Drudging (donning my obnoxiously cheery rain boots and running tights while fighting with my umbrella for the entire walk) my half-hung-over self (give me a break, this happens once in a blue, or in this case, full moon) to the gym for a good kick-in-the-ass workout, I was thinking about dinner. What would be delicious, but easy? And a sure cure for feeling bleu? Gooey, crispy pan-friend grilled cheese and creamy tomato soup. Done.

Cast iron pan, meet grilled cheese.

And what's better: turning the oven on will heat your kitchen, the soup will make it smell amazing, and the aroma of a grilled cheese will top it off.

You should probably make a point of swinging by the grocery store tonight and grabbing the stuff you need to make this. Heck, you may even have most of it already-and besides, stocking up on canned tomatoes (or even homemade, if you're lucky, like I am) is probably a good idea for the impending chili season.

So go ahead…make my day…and make yourself a treat. You deserve it.

Creamy Tomato Soup
Makes enough for 4 generous servings

Ingredients:
Two 28oz cans of whole tomatoes, drained with 3 cups juice reserved
1 1/2 teaspoons brown sugar, white sugar or honey
2 TB butter
2 TB olive oil (or, 4 TB total butter)
2 clove garlic, smashed
1/2 small onion or 2 shallots, finely diced
2 TB flour
1 1/2 cups stock (vegetable or chicken)
1 1/2 cups milk (any kind will do)
2 TB tomato paste
pinch allspice or nutmeg
salt and pepper to taste

For the grilled cheese:
Slices of your favorite semi-squishy bread, such as a sliced sourdough, italian loaf or even white sandwich bread
Any combination of favorite cheeses, preferably meeting the trifecta of ooey-gooey (like gouda), sharp and salty (aged cheddar*) and pungent (gorgonzola or any bleu cheese), all thinly sliced, or grated, or crumbled
Olive oil or butter

*I was lazy, and opted for the pre-shredded cheddar. I mean, I was making the tomato soup from scratch, I am allowed a cop-out.

Equipment:
Baking sheet
Aluminum foil
Medium to large pot
Wooden spoon
Whisk
Knife
Cutting Board
Immersion blender or regular blender
Large pan
Spatula

Method:
Pre-heat your oven to 450F. Strain the tomatoes using a strainer or carefully by using the lid of the can, but reserve 3 cups of the juice. Using your hands, squeeze out the seeds from the tomatoes, and place on the aluminum foil lined baking tray.

Reserved tomato juice and milk make for an awesome tomato-y and creamy soup

Sprinkle the tomatoes with the brown sugar, white sugar or honey, and gently toss to coat. Bake for 30 minutes, until the juices are mostly evaporated and there is slight browning on the tomatoes lining the edges of the sheet. Allow to cool.

The foil will make life way easier when it comes to peeling' this babies off the pan

While the tomatoes bake, get on with the rest of the soup: heat the oil and/or butter in a medium to large pot. Add the onions or shallots, and the smashed garlic. Cook over medium until tender, about 5 minutes. Add the tomato paste and the flour, and stir to combine. Cook (what is now a roux) until the flour is slightly brown, about 3 minutes over medium.

Slowly add the stock, then the milk, then the tomato juice, whisking constantly. Now, peel the tomatoes from the baking sheet, and add to the pot. Turn the heat to medium-low, cover, and let the mixture cook for about 20 minutes.

Take the pot off the heat, and puree with an immersion blender or transfer with a coffee cup in batches to a regular blender. Return the soup to low heat, and cover.

Now, make the grilled cheese: pre-heat a pan on medium heat, and add the olive oil and/or butter. Slice the cheeses, or sprinkle if cheating and using pre-shredded. Layer the cheeses on a slice of bread, then transfer to the warmed pan. Cover, and allow the cheese to melt and the bread to brown-about 5 to 10 minutes depending on your pan, bread thickness, cheese variety and stove-top. Check occasionally-no one likes a burnt grilled cheese…when the bread is browned and the cheese is melted, add slices of bread atop the melted cheese and flip. You may need move the bread around a bit to sop-up the olive oil or butter. Cover, and brown the bread.

Remove the grilled cheese from the pan, and slice in half (if desired-I personally think triangle shapes aid in dipping). Let sit for a moment while you dish up the soup. Serve hot, with or without some sort of green vegetable to make you feel like you are consuming a well-balanced meal, such as steamed green beans with sea salt, garlic and olive oil. If you have pesto hanging around, it'd probably be a good idea to put a small dollop on top of the soup, as we did.