How to Make a Killer Grilled Cheese Sandwich, with Tomato Soup to Match
Cheddar vs. American cheese? Fresh vs. canned tomatoes? Get tips and recipes for the best grilled cheese and tomato soup ever, and treat yourself to the ultimate comfort food combo.
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Quick and Creamy Tomato Soup and Oven-Baked Classic Grilled Cheese Sandwiches. Photograph by Olga Ivanova.
I’m a late-comer to the grilled cheese appreciation society. When I was a kid I hated cheese — the only way I could tolerate it was on pizza or in mac and cheese. So even though my mom made what must have been quite a tasty toastie, I’d never even let one touch my plate, saving all my affection for the glorious tomato soup she served alongside. I didn’t start eating grilled cheese until college. That’s when I discovered what a perfect weeknight dinner the soup + sandwich combo makes, with minimal prep time yielding maximum pleasure. To me, the act of pulling apart the two halves of a sandwich fresh from the pan, watching the cheese stre-e-e-tch between the golden toast before it gets a hearty dunk in the soup, is almost as satisfying as eating it. Almost.
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Keys to a killer grilled cheese sandwich
I’m not saying it’s hard to make a grilled cheese sandwich — but making a memorable one, the kind that will send you back to the kitchen to make another while you’re still chewing the first, takes some finesse.
Let’s talk about ingredients first:
The fat. You won’t achieve that perfectly browned exterior without a little something to get things sizzling. My earliest sandwiches always used unsalted butter, but as an adult I’ve been seduced by mayonnaise. It has a higher smoke point than butter, which means you’re less likely to burn the outside before the cheese is melted. Plus, you can spread it on a slice of bread right out of the jar — no need to leave it on the counter to soften.
The bread. Traditionally, grilled cheese calls for white bread, and a sandwich made with two slices from a supermarket loaf can be really good. But it’s so much better when you have some fun. Thickly sliced white bread from a bakery is an easy upgrade, and so is sourdough bread. One of my favorite grilled cheese experiments involved pumpernickel bread, white cheddar, bacon, and a drizzle of hot honey. As long as the slices are on the dense, sturdy side, you can use whatever you like.
The cheese. You literally can’t make a grilled cheese without it, so you might think your choice of cheese would need to be fairly precise. But I don’t think so. You do need something melty — in my family, we use mostly cheddar cheese (my go-to), mozzarella (my kid’s fave), or American cheese (my husband’s choice when he’s feeling nostalgic), but I’ve also made some primo variations with gruyere, manchego, fontina, havarti, and gouda. And sometimes for fun, I’ll sprinkle a little freshly grated Parmesan into the skillet before I add the bread. It adheres to the butter side and makes an extra-crunchy, extra-savory crust.
The extras. You can make a pretty memorable grilled cheese with just those three items, but hoo-boy do things get good when you add a little something. The recipes that follow will give you ideas, but don’t be afraid to play around. (Pro tip: Grilled cheese sandwiches are an excellent way to use up leftovers.)
Now let’s talk technique. You’ll find recipes below using the oven, air fryer, or panini press, but I’m faithful to the stovetop:
Basic grilled cheese. Heat a large skillet or griddle over medium-low heat. Spread fat on one side of each slice of bread. If you’re making a simple sammich, put the bread in the pan butter-side down and top with your chosen cheese. Add the remaining bread, butter-side up, and cook for 3-4 minutes per side, until the outside is golden brown and the cheese is melted. Got more than cheese going on? Assemble the sandwiches before putting them in the skillet, so you don’t burn the bread while piling everything on.
Keys to killer tomato soup
There’s no better accompaniment to grilled cheese than a steaming bowl of homemade tomato soup made right.
Let’s start with ingredients:
Fresh vs. canned tomatoes. At the height of summer, fresh tomatoes scooped up at the farmer’s market (or grown in the backyard) can’t be beat, but much of the time, canned tomatoes have more concentrated flavor. If you have the option, try canned San Marzano tomatoes, an Italian variety known for its low acidity and vivid tomatoeyness (that’s a word, right?).
Aromatics. At the minimum you’re going to need some onion, garlic, and an herb like thyme or parsley.
Broth. Either some chicken broth or vegetable broth will add to the savory flavors.
As for techniques, making tomato soup couldn’t be simpler:
Basic tomato soup. Grab a large pot and saute some aromatics like yellow onion in olive oil until soft. Add cans of tomatoes plus several cups chicken stock or vegetable broth and some dried or fresh herbs, and simmer. Carefully puree with an immersion blender or regular blender, adjust the seasoning with salt and black pepper, and serve.
Best grilled cheese and tomato soup recipes
Whether you’re looking for dinner recipes or just a way to mix things up a little, you’ll find your new favorite grilled cheese here — as well as the perfect tomato soups to serve alongside.
Classic grilled cheese sandwiches
Sometimes, you want a grilled cheese sandwich like your mom made. Only better.
White bread, cheese, butter, and mayo are all you need to make the grilled cheese sandwich of your dreams. With tips about technique, choice of cheese, and more, this can be your base recipe, the one where all future grilled cheese sandwiches will begin.
If you’re making grilled cheese for the family, one-by-one in a skillet will take a while. This smart recipe gives you six gooey sandwiches at once, with a hack that gets them golden brown on both sides, no flipping required.
My kid loves to make his own grilled cheese, but he gets impatient and sets the burner at medium-high heat. You can guess what happens: Burned toast, not-quite-melted cheese. But making grilled cheese in an air fryer ensures it’s perfectly toasted every time.
Savory grilled cheese sandwiches
Think of these recipes as grilled cheese taken up a few notches. Each one has something added, an extra bit of umami to keep things interesting.
The grilled cheese sandwich at London’s Borough Market is world-famous, and rightly so. It might be the tastiest sandwich I’ve ever eaten. This recipe recreates it with two types of cheese, three types of allium (leeks, red onion, and garlic), and sourdough bread.
I feel like I should add a disclaimer here: Putting portobello mushrooms and spinach on a grilled cheese sandwich doesn’t make it any less indulgent. In fact, with three kinds of cheese, this beauty feels like something you’d serve at a cocktail party. Y’know, like a stuffed mushroom.
Don’t let the plain-Jane name fool you. Burnished caramelized onions, fresh herbs, and three types of cheese pack tons of flavor between two slices of sourdough bread. Pro tip: Next time you’re caramelizing onions for a recipe, add an extra onion or two to the pan to use here.
Meaty grilled cheese sandwiches
Sometimes, you want a little more heft in your grilled cheese. Enter these two-handed sandwiches. One of these is definitely enough for dinner.
If you love sloppy Joes and you love grilled cheese, this might be the most exciting idea ever. Yes, it’s exactly what it sounds like — homemade sloppy Joe filling and American cheese between slices of white bread — but it’s so much more than the sum of its parts.
Next time you make (or buy) pulled pork, be sure to set aside a few cups — you’ll need one cup per sandwich to make this gorgeous beast. Pro tip: Before assembling, reheat the meat with some good-quality barbecue sauce, the smokier the better.
This handful is rocking three kinds of cheese and three types of Italian deli meat, plus a red wine vinaigrette, sun-dried tomatoes, red onion, and tomato sauce. I’m not kidding when I say it’s a whole meal.
Sweet & salty grilled cheese sandwiches
I probably should’ve put this category first, since it’s my favorite. I’m a big fan of playing a hint of sweetness off the salty cheese.
Just the name of this one has me salivating. The raspberry part comes in the form of raspberry preserves, spread on one slice of bread before everything else gets piled on top. And how about that everything else? Sliced pear (yum), crispy bacon (whoa), and buttery muenster (oh yes).
Here’s a way to turn ordinary deli turkey into something spectacular. Each sandwich gets a smear of apple butter and a little fresh sage, plus some good sharp cheddar and thinly sliced apple. If you ask me, it’s the fresh sage that really takes this over the top.
Love, love, love the idea of using cinnamon swirl bread for grilled cheese. And the combination of tangy goat cheese, sweet fig jam, and peppery arugula is just perfect. This, right here, is a grown-up grilled cheese.
Perfect tomato soup recipes
There’s no better accompaniment to grilled cheese than a steaming bowl of homemade tomato soup. Even with the basic formula, there are variations.
Basil and roasted red peppers enhance the sweetness of canned San Marzano tomatoes, and a smidge of balsamic vinegar brings it all into balance. All you do here is saute the onion and aromatics, simmer them with tomatoes and broth, and give it a blitz with a blender. A modest splash of cream at the end enhances the silky texture.
If you lean towards the rich-and-luscious in your tomato soup preferences, look no further. This recipe gets thickened twice: first, by making a roux with flour, olive oil, and butter, which adds body while the soup simmers, and then with a cup of heavy cream, stirred in at the very end.
Most grilled cheese doesn’t take long to prepare — that’s why it’s such a perfect I-don’t-know-what-to-cook dinner. If you’re in a time crunch, give this recipe a look. The total time is just 15 minutes. It gets its creaminess from pureed white beans, keeping it solidly in vegan territory.
If you’ve got a little time on your hands, this recipe will knock your socks off. It uses two kinds of tomatoes — fresh plum tomatoes, which you roast with garlic cloves to intensify the flavors, and canned San Marzanos. With fresh basil, oregano, and thyme, crushed red pepper flakes, and chicken broth, the soup is satisfying even without a grilled cheese sandwich.
Explore more soups and sandwiches
When comfort food cravings hit, reach for one of these additional recipes.