Smoky Roasted Tomato Soup with Grown Up Grilled Cheese
I have always had a soft spot for tomato soup and a grilled cheese sandwich. It is the sort of lunch that asks very little of you, other than finding a comfortable chair and perhaps putting the kettle on afterwards.
Growing up in Liverpool, tomato soup usually arrived from a tin, accompanied by thick slices of buttered bread. There was nothing particularly sophisticated about it, but on a cold, wet afternoon, it was exactly what you wanted.
These days, I like to give that familiar combination a little more attention.
TIME 1 hour 30 minutes | SERVES 4 | LEVEL Easy |
BEFORE YOU START This soup starts with finely minced shallots and finishes with careful tasting and seasoning. Both are covered in my Kitchen School, and each lesson takes about five minutes to read. |
Why You'll Love It
ROASTED CANNED TOMATOES Deep, concentrated flavour all year round | SMOKE AND BRANDY Gentle smoky warmth with a rich finish |
THREE-CHEESE GRILLED CHEESE Gruyère, Brie and mature cheddar, with crisp bacon | MAKES AHEAD The soup keeps for up to three days |
Tested in my kitchen · As seen on TODAY and The Tonight Show · Parade magazine's chef for 10 years · About Chef Jon → |
Smoky Roasted Tomato Soup with Grown Up Grilled Cheese
Serves 4 | Prep: 30 minutes | Cook: 1 hour | Total: 1 hour 30 minutes
Ingredients
For the Smoky Roasted Tomato Soup
2 cans (28 oz / 794 g each) whole peeled tomatoes, preferably packed in juice
1½ tablespoons dark brown sugar
4 tablespoons (56 g) unsalted butter
4 large shallots, finely minced
1 tablespoon tomato paste
A small pinch of ground allspice
2 tablespoons all-purpose flour
2 teaspoons smoked paprika
1¾ cups (420 ml) chicken stock
½ cup (120 ml) heavy cream (double cream)
2 tablespoons brandy or dry sherry
A pinch of cayenne pepper, to taste
Fine sea salt, to taste
Freshly ground black pepper, to taste
For the Grown Up Grilled Cheese
4 ounces (115 g) Gruyère cheese, grated
2 ounces (55 g) Brie, rind removed
3 ounces (85 g) sharp (mature) cheddar, grated
2 slices bacon, cooked until crisp
2 tablespoons dry white wine or dry vermouth
4 teaspoons finely chopped fresh chives
3 tablespoons (42 g) unsalted butter, softened
1 teaspoon Dijon mustard
8 slices hearty rye sandwich bread
Instructions
STEP 1 OF 15
Heat the oven
Preheat the oven to 450°F (230°C). Position a rack in the upper middle section of the oven.
STEP 2 OF 15
Drain and seed the tomatoes
Drain the canned tomatoes over a bowl, reserving all their juices. Gently open each tomato and remove the seeds where practical. There is no need to be overly meticulous.
STEP 3 OF 15
Roast the tomatoes
Arrange the drained tomatoes in a single layer on a foil lined, rimmed baking sheet. Sprinkle evenly with the dark brown sugar.
Roast for approximately 30 minutes, until much of the moisture has evaporated and the tomatoes have developed deep golden edges. You want them slightly caramelised, with a rich, concentrated flavour.
You'll know it's right when most of the liquid has gone and the tomatoes have deep golden, slightly caramelised edges. |
STEP 4 OF 15
Lift off the tomatoes
Remove the tomatoes from the oven and allow them to cool slightly. Carefully lift them from the foil, scraping up any delicious caramelised juices, and set aside.
STEP 5 OF 15
Soften the shallots
Melt the butter in a large, heavy saucepan over medium heat. Add the minced shallots, tomato paste and a small pinch of allspice.
Reduce the heat to low, cover, and cook gently for 7 to 10 minutes, stirring occasionally, until the shallots are soft and sweet. Take care not to brown them.
You'll know it's right when the shallots are soft, sweet and translucent, with no brown edges. |
STEP 6 OF 15
Add the flour and paprika
Stir in the flour and smoked paprika. Cook for approximately 1 minute, stirring constantly, until the flour loses its raw aroma and the paprika becomes fragrant.
STEP 7 OF 15
Simmer
Gradually whisk in the chicken stock, followed by the reserved tomato juices. Add the roasted tomatoes and any juices collected from the roasting tray.
Bring the soup to a gentle simmer, then reduce the heat and cook for approximately 10 minutes, stirring occasionally. The flavours will begin to deepen, and the soup will thicken slightly.
STEP 8 OF 15
Blend
Remove the saucepan from the heat. Using an immersion blender, blend the soup until smooth. For a particularly velvety texture, transfer it to a countertop blender in batches, taking care with the hot liquid.
If you prefer an exceptionally smooth soup, pass it through a fine mesh sieve, pressing gently to extract as much liquid as possible.
Chef Jon's tip: if you use a countertop blender, fill it no more than halfway and hold the lid down with a folded kitchen towel. Hot soup expands as it blends. |
STEP 9 OF 15
Finish with cream and brandy
Return the soup to the saucepan and stir in the cream. Warm gently over low heat for approximately 3 minutes, without allowing it to boil vigorously.
Stir in the brandy or dry sherry and allow the soup to simmer gently for another 2 minutes. This softens the sharper alcoholic notes while retaining the lovely aromatic character.
STEP 10 OF 15
Season
Season with fine sea salt, freshly ground black pepper and a little cayenne pepper. Taste carefully. The soup should have a pleasing balance of sweetness, acidity, gentle smokiness and richness.
Keep warm over very low heat while preparing the grilled cheese sandwiches.
You'll know it's right when the soup tastes sweet, bright, gently smoky and rich all at once, with no single flavour shouting. |
STEP 11 OF 15
Make the cheese spread
Place the grated Gruyère, Brie, cheddar and white wine into a food processor. Pulse for approximately 20 to 30 seconds, until the cheeses form a thick, spreadable mixture.
Add the finely chopped chives and pulse briefly to incorporate. You want the chives distributed throughout the cheese rather than completely puréed.
STEP 12 OF 15
Make the mustard butter
In a small bowl, combine the softened butter and Dijon mustard, stirring until smooth.
Arrange the rye bread slices on a clean work surface. Spread one side of each slice with a thin, even layer of mustard butter.
STEP 13 OF 15
Assemble the sandwiches
Turn four slices over so the buttered sides face down. Divide the cheese mixture evenly between them, spreading it generously across the bread.
Break the crisp bacon into pieces and scatter over the cheese mixture.
Place the remaining slices of bread on top, with the buttered sides facing outward. Press gently to secure the sandwiches.
STEP 14 OF 15
Cook low and slow
Heat a large, heavy frying pan over medium heat for approximately 2 minutes.
Place two sandwiches into the pan and immediately reduce the heat to medium low. Cook gently for approximately 4 to 6 minutes on the first side, until the bread is golden brown and crisp.
Carefully turn the sandwiches using a spatula and cook for another 4 to 6 minutes, until the second side is golden and the cheese has melted completely. Adjust the heat as necessary. The bread should toast slowly enough to allow the cheese to become beautifully molten.
You'll know it's right when both sides are deep golden and crisp, and the cheese is oozing at the edges. |
If something's off: if the bread is browning before the cheese melts, turn the heat down and give it another minute or two each side. |
STEP 15 OF 15
Rest, slice and serve
Transfer the sandwiches to a chopping board and allow them to rest for 1 to 2 minutes before slicing. Repeat with the remaining sandwiches.
Cut each sandwich diagonally and serve immediately alongside a warm bowl of smoky roasted tomato soup.
Tips & Chef's Notes
Don't be overly meticulous when seeding the tomatoes. Remove the seeds where practical and move on.
Start with one teaspoon of smoked paprika if you prefer something more delicate. Use a good quality Spanish smoked paprika if possible.
Give the soup a brief simmer after adding the brandy or sherry, so the flavours become properly integrated.
Cook the sandwiches over a gentle heat. Patience is the secret to a magnificent grilled cheese.
Made it? I'd love to see it
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Key Ingredients
Canned Whole Tomatoes: Good canned tomatoes are available all year, and roasting turns them deep and concentrated.
Dark Brown Sugar: Encourages gentle caramelisation and softens some of the acidity.
Shallots: Cooked slowly in butter until soft and sweet.
Smoked Paprika: A gentle, woodsy smokiness that complements the roasted tomatoes.
Brandy or Dry Sherry: Brandy adds warmth and richness; dry sherry brings a nutty complexity.
Gruyère, Brie and Mature Cheddar: Nutty, creamy and sharp, in that order.
Rye Bread: Hearty enough to hold a generous filling and toast to a crisp, golden crust.
Mustard Butter: A gentle sharpness that balances the richness of the cheese and bacon.
Why I Roast Canned Tomatoes
I know what you might be thinking. Why go to the trouble of roasting tomatoes that have already been cooked and canned?
Because roasting changes them rather dramatically.
As the moisture evaporates, the tomato flavour becomes more concentrated. The brown sugar encourages gentle caramelisation, softening some of the acidity and developing a richer, almost savoury sweetness.
It is a simple technique that makes an enormous difference. And because good canned tomatoes are available throughout the year, you can enjoy this soup even when fresh tomatoes are little more than a distant summer memory.
Chef's Secret: Smoked Paprika and a Splash of Brandy
I prefer smoked paprika to ordinary sweet paprika in this recipe. It brings a gentle, woodsy smokiness that complements the roasted tomatoes beautifully.
Two teaspoons provide a noticeable smoky character, although you can begin with one teaspoon if you prefer something more delicate.
Brandy and dry sherry both work beautifully, although they bring slightly different personalities to the soup. Brandy adds warmth and a subtle richness, while dry sherry introduces a lovely nutty complexity. I particularly enjoy dry sherry here, especially when the soup is served with the Gruyère and Brie sandwich.
The Secret to a Magnificent Grilled Cheese
Patience.
A grilled cheese sandwich cooked over fierce heat will often produce beautifully browned bread with a disappointing lump of unmelted cheese in the middle. I prefer a gentle heat and a little more time.
The rye bread gradually develops a crisp, golden crust while the cheese softens into a rich, creamy filling. The small amount of wine in the cheese mixture adds flavour and helps create a smooth, spreadable filling before cooking.
And don't forget the mustard butter. It brings a gentle sharpness that balances the richness of the cheese and bacon.
Why Three Cheeses?
Each cheese has a purpose. Gruyère brings a deep, nutty flavour and melts beautifully. Brie contributes a luxurious creaminess. Mature cheddar provides a pleasant sharpness that keeps the sandwich from becoming overly rich.
Together, they create a filling that is far more interesting than any one cheese could achieve alone.
Common Mistakes to Avoid
Skipping the roast: the soup will taste thinner and sharper without it.
Browning the shallots: cook them low and covered so they stay soft and sweet.
Boiling after the cream goes in: keep it at a gentle warmth so the soup stays silky.
Rushing the grilled cheese: high heat burns the bread before the cheese melts.
Over-processing the chives: pulse briefly so they stay as green flecks.
Twists to Try
Make it vegetarian: use vegetable stock and leave out the bacon.
Without alcohol: leave out the brandy and finish the soup with a few drops of sherry vinegar instead.
Swap the bread: thick sourdough makes an excellent grilled cheese too.
A little heat: add an extra pinch of cayenne, or a few chilli flakes with the paprika.
What to Serve with Tomato Soup
The grown up grilled cheese, of course, cut on the diagonal for dipping
A crisp Greek Salad
A tray of Tomato Focaccia
A Croque Monsieur for a change of sandwich
How to Store
Fridge: The soup can be prepared up to three days in advance and stored in an airtight container in the refrigerator. Reheat gently over low heat, stirring occasionally. If it has thickened, add a little chicken stock until you reach your preferred consistency.
Make ahead: Prepare the grilled cheese sandwiches just before serving. They are at their best when the bread is crisp and the cheese is still warm and melting. The cheese spread can be made a day ahead and kept covered in the fridge.
Freezer: Freeze the soup before adding the cream, for up to 3 months. Thaw overnight in the fridge, reheat gently, then stir in the cream and brandy.
Frequently Asked Questions
Why roast canned tomatoes?
Roasting evaporates moisture and concentrates the tomato flavour, while the brown sugar encourages gentle caramelisation. It is a simple step that makes an enormous difference.
Can I use fresh tomatoes?
You can, although I prefer canned here. Good canned tomatoes are available throughout the year, and roasting them gives the soup a deep, concentrated flavour.
Brandy or sherry?
Both work. Brandy adds warmth and richness, while dry sherry brings a nutty complexity. Simmer briefly after adding either.
Can I make the soup without alcohol?
Yes. Leave it out, or finish with a few drops of sherry vinegar for a little lift.
Can I make it vegetarian?
Use vegetable stock in the soup and leave the bacon out of the sandwiches.
Do I need a food processor for the cheese?
It makes the smoothest spread, but you can grate the cheeses finely and mash them with the Brie, wine and chives in a bowl.
Can I freeze tomato soup?
Yes, for up to 3 months. Freeze it before adding the cream, then stir the cream in when reheating.
What is the best bread for grilled cheese?
A hearty rye or sourdough sandwich loaf that holds its shape and toasts to a crisp crust.
The Story Behind This Soup
The tomatoes are roasted until their edges begin to caramelise, concentrating their sweetness and giving the soup a lovely depth. Shallots soften slowly in butter, smoked paprika adds a gentle warmth, and a splash of brandy brings a richness that is difficult to put your finger on.
A little cream rounds everything off, leaving you with a soup that is smooth, velvety, and full of roasted tomato flavour.
And then there is the sandwich.
I use three cheeses. Gruyère for its wonderful nuttiness, Brie for its creamy richness, and a good mature cheddar for that familiar sharpness. A little white wine helps bring everything together, while fresh chives add a delicate onion flavour.
There is also bacon. Crisp, salty bacon.
The bread is rye, generously spread with butter and a little Dijon mustard, then toasted slowly in a pan until the crust is golden and the cheese inside has melted into something quite irresistible.
I like to cut the sandwiches diagonally, exposing all that molten cheese, and serve them alongside a generous bowl of soup.
The first bite is always rather good.
But dipping the corner of that crisp sandwich into the warm tomato soup is where the real pleasure begins.
The Last Spoonful
I have eaten some rather elaborate lunches over the years, in beautiful restaurants and in places where the tablecloths are so white you almost feel guilty putting your elbows on them.
But I would happily trade a good many of them for a bowl of tomato soup and a properly made grilled cheese sandwich.
Particularly on a cold afternoon, when the rain is tapping against the kitchen windows and there is nowhere you particularly need to be.
The soup is warm, rich, and gently smoky. The bread is crisp, the cheese is melting, and there is always that last little corner of sandwich waiting to be dipped.
I suspect I will never tire of it.
And I rather hope you won't either.
Recommended Equipment
Make this recipe easier with the right tools: Rimmed Baking Sheet, Sauce Pan, Hand Held Blender, Food Processor, and Cast Iron Skillet. Also useful: Blender.
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