Food is comforting to me, in general, but this may be the ultimate comfort food. There’s a reason that Grilled Cheese and Tomato Soup is a ubiquitous pairing. The acidity of the tomatoes balances the richness of the sandwich. Rich, cheesy, buttery, a little sweet, a little acidic… everything is right with the world. It’s a little bit sinful, but the mostly-healthy soup evens that out… right? Sure. Let’s go with that.
As much as I like my Dad’s little processed cheese miracle (Velveeta, yellow mustard and white bread – honestly, it’s fantastic), that’s not the sandwich I’m making if I’m having it with this tomato soup. This one needs to stand up to a deeply flavorful tomato bisque – so I’m making it with thick crusty sourdough bread, cheese that doesn’t have quotation marks around it on the packaging, and caramelized onions. Oh yes. Caramelized. Onions.
- 2 – 28 oz cans whole San Marzano tomatoes
- 1 – 28 oz can crushed tomatoes
- 2 shallots, quartered
- 4 cloves garlic, whole, skin on
- 1 Tbsp. extra virgin olive oil
- 1 tsp dried oregano
- 10-ish thyme sprigs
- 1 clove garlic, minced
- 3 Tbsp. unsalted butter
- ½ tsp crushed red pepper flakes
- 1 Tbsp. tomato paste
- 2 Tbsp. Dry Sherry
- 1-2 cups chicken or vegetable stock
- ¼ cup heavy cream
- Salt and pepper, to taste
Caramelized Onion Grilled Cheese
- Crusty Bread in 1/2 thick slices – sourdough is preferred
- Butter (Or – try mayo!)
- 4-6 slices of Swiss cheese per sandwich
- 2-3 TBS caramelized onions (recipe follows)
Preheat oven to 400°. Line a rimmed sheet tray with parchment paper.
Drain the whole tomatoes and add to a large bowl with the quartered shallots and whole garlic. Drizzle with olive oil and season with salt, pepper and oregano, toss to coat, and then transfer the bowl’s contents to the sheet tray with a slotted spoon. Arrange the thyme sprigs on top and around the veggies. Roast in the top third of the oven for 30 minutes, then remove and set aside until cool enough to touch. Remove skins from garlic and shallots, discard with the thyme sprigs.
Heat a large dutch oven over medium heat, and when warm add butter. When butter foams, add minced garlic and red pepper flakes, stirring for about one minute, until fragrant but not brown. Add tomato paste and stir to mix with the butter and garlic, allowing it to slightly caramelize for one or two minutes. Deglaze the pan with sherry, cooking off the alcohol and most of the liquid.
Add roasted veggies to the pot along with the crushed tomatoes and one cup of chicken stock. Season with salt and pepper, and simmer for 15 minutes.
Puree the soup until smooth with either with an immersion blender, or in a standard blender in batches. Work carefully with hot soup in a blender – it can very easily blow out the top. I find working in small batches, giving it plenty of air space, works best. I’ve also been known to vent it by removing the center hole lid, you know, where you can stick in a plunger to move things around? Then I cover the hole with a kitchen towel to prevent any potential splashes, while still allowing heat and steam to escape freely.
Stir in cream and assess the consistency of the soup, adding more chicken stock to thin the soup if necessary, to your liking. Taste for seasoning and adjust with salt.
Heat a griddle or large nonstick skillet over medium heat. Coat one side of each bread slice with butter. Layer the inside of the sandwich as follows: bread (butter side out), 2-3 slices of cheese, overlapping, a layer of caramelized onions, 2-3 slices of cheese, bread (butter side out).
Cook your sandwiches on moderate heat, allowing the cheese to drip down and create those awesome lacy crusty cheese edges, until golden and crispy on both sides and melty in the middle. Cut diagonally – it’s better for dipping in the soup.
Slice 4 large sweet or yellow onions thinly – consistency is key. (Walla Walla sweets preferred, but unless you are in the Northwest, you won’t find them. Yellow is fine. Vidalia is great too.)
Add a few tablespoons of butter to the largest skillet you have – it needs a lid. (Although you could probably make aluminum foil work!) Melt the butter until foaming, then add the onions a little at a time, tossing to coat with the butter. I find letting them soften in stages makes it easier to get them all coated and all in the pan. When everybody is in the pot, season with a pinch of salt, turn the knob to medium low and put the lid on. Cook in 3-5 minute intervals, stirring occasionally, until the onions are uniformly softened and translucent. Then, remove the lid and continue cooking, stirring more and more often as the onions continue to cook and begin to caramelize. Toward the end, they will require more attention. Don’t let the onions burn. Set a timer for every 10 minutes if you need to. (I do, because I will get distracted in a long process.)
When the onions are uniformly caramel colored, reduced by at least 1/4 and have become jammy, you can call them done. You can keep cooking as long as you would like, or you can leave them here. Store any unused onions in the fridge up to 5 days or vacuum sealed in the freezer for 1 month.
QUICK Caramelized Onions: The weeknight cheat
Use the same process as above, but continue cooking with a lid until the onions are very soft. At that point, remove the lid and add 1 Tbsp. of balsamic vinegar and stir while simmering until the liquid from the onions and vinegar cooks off. Taste, adding more vinegar for sweetness if necessary, and repeating the process of cooking off the liquid.