Roasted Tomato Soup and Grilled Cheese

Roasted Tomato Soup and Grilled Cheese

by BiteSizedJessica on October 6, 2010

I’ve come to believe grilled cheese is one of those measures of your ability as a cook. It’s not just that grilled cheese is so great, everyone knows this. But I see a grilled cheese sandwich the way many people see the challenge of cooking the perfect egg or making a really, truly good soup – that it’s the test of your abilities in the kitchen, and Jon feels the same way.

Like an egg, grilled cheese can be so simple – just cheese and bread. But there’s a fine line between an over cooked egg and a perfectly cooked one – just as there’s a fine line between the right amount of cheese and the perfectly browned, buttery toast versus unmelted cheese or soggy bread. And like a good soup, putting a few subtle extra ingredients into the grilled cheese can take it to a new height and make it unique, while the person eating it doesn’t even know those secret ingredients are there. Making grilled cheese around here isn’t just for fun – it’s also become a source of pride, and as a result, a competition.

Anyone who’s played charades with me knows that entering into a competition with me is a play at your own risk situation. But Jon is a brave man, and a few years ago, we had a grilled cheese competition to see who could make the best sandwich. We invited a few impartial judges (our two best friends) and had three rounds of sandwiches going head to head, with just two rules – 1. 4 ingredient limit, not including bread; 2. Sandwich must involve cheese and bread. I won the showdown by a narrow margin, which Jon still contests as being unfair due to the order in which we served our sandwiches (he’s wrong).

Now that I’ve been named the master of grilled cheese, we are able to make them together or for each other without contention or fear of a brawl. We have a few different breads we like to use for grilled cheese. Sometimes it’s the dinner rolls from Amy’s Bread that I get at work. Sometimes it’s a ciabatta loaf from Veneiro’s Italian specialty shop. But the best is the Challah loaf we get from B&H. We also have a variety of toppings for grilled cheese, and whatever they are – sautéed onions, pesto, chimichurri, tomato salad, ham, an over-easy egg, avocado, turkey, fresh sliced tomato and onions, hot sauce, ranch dressing, or our special homemade mayonnaise – multiple grilled cheeses with different sauces and toppings often become a full meal for us.

These past few dreary, cold days gave me the chills and grilled cheese dipped in soup was pretty much the best meal I could imagine. We used the B&H Challah and roasted the tomatoes before putting them in the soup, to bring out more of their sweetness. The soup was thick, bright and rich despite its few simple ingredients, as was the grilled cheese. Combined they were a familiar but fantastic combination.

(Makes 1 quart of soup and lots of mini grilled cheeses)

To Roast Tomatoes:

2 large hothouse tomatoes
3 plum tomatoes
5 cloves garlic
1 small bunch thyme
½ cup olive oil
Salt and Pepper
Red pepper flakes

For the Soup:

2 tbsp butter
3 whole canned tomatoes, plus juices
3 shallots
2 cloves garlic
1 cup chicken stock
¼ cup heavy cream

For the Grilled Cheese:

1 tbsp butter
½ loaf Challah bread
¼ lb Jarlsberg cheese


1.    To roast the tomatoes, start by removing the core from the top. Halve the tomatoes and place them cut side down in a glass casserole dish.

2.    Add 1 sliced shallot and 5 cloves of crushed garlic to the pan, along with the sprigs of thyme. Season with salt and pepper, and sprinkle with red pepper flakes.

3.    Coat well with olive oil. Cover casserole with foil and roast at 500° for 20-30 minutes, until tomatoes are soft.

4.    When oil has cooled, remove tomatoes, thyme and garlic. Discard thyme and chop the roasted garlic, along with two additional raw cloves. Reserve the tomato juices and olive oil that have gathered in the bottom of the pan.

5.    Thinly slice remaining two shallots. In a large pot, heat 2 tablespoons of butter. Sweat garlic and shallots until softened. Let them brown a little on the bottom of the pan. When browning occurs, use the reserved tomato juices to deglaze and scrape everything up.

6.    Add in roasted tomatoes, canned tomatoes, tomato juices and chicken stock. Bring up to nearly boiling and then reduce to a simmer. Cook until tomatoes are very soft, about 30 minutes.

7.    Puree the soup in a food processor or blender. Add back into the pot and finish seasoning with salt and pepper to taste. Add in cream and adjust the soup’s consistency with stock and / or water, if necessary. Serve hot with the grilled cheese.

8.    To make the grilled cheese, cut the bread and cheese to desired size. Heat a small pan with butter and put sandwich in, open faced, with cheese on both sides. When you want to get the cheese really nice and melted, toss a teaspoon of water into the hot pan, then quickly cover with a lid. Leave closed for 30 seconds and, when you remove the lid, the cheese will be melted and bread will be browned. If not, repeat water steaming process, making sure butter doesn’t burn in the pan. Close the sandwich and eat hot, with hot soup, on rainy day.

© 2010 Jonathan Meter and Jessica Hertle

{ 9 comments… read them below or add one }

Chocolate Shavings October 6, 2010 at 12:43 pm

Now that’s a grilled cheese!

Julia October 6, 2010 at 4:13 pm

Oh yum, seriously! That’s it, that’s all I have to say 🙂

Aditi Mulgund October 6, 2010 at 5:01 pm

This looks delicious! I actually love roasting tomatoes and putting them IN the grilled cheese. I made a bunch as an appetizer once!

christelle is flabbergasting October 6, 2010 at 8:53 pm

This looks absolutely delicious!

Sarah October 6, 2010 at 9:42 pm

What beautiful photography! You really know how to take something simple and unintimidating and turn it into a work of art! Also…can i come over for lunch? 😉

Foodie McBody October 7, 2010 at 12:31 am

Heartstoppingly beautiful. YUM.

BiteSizedJessica October 7, 2010 at 12:42 am

Thanks everyone for your comments and compliments.

Fritos and Foie Gras – thanks for the acknowledgement! That’s pretty much my goal a lot of the time when I cook, so I’m glad to hear it translates.

Aditi – roasted tomatoes in the grilled cheese is a great idea and one I actually haven’t tried. As an appetizer it must be delicious.

It’s so nice to hear all of your responses! And thanks for checking out our site.

Emma October 8, 2010 at 1:13 pm

Loving the presentation on the top piccie – grilled cheese gets the Michelin starred treatment! 🙂

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