Soup and sandwich, an infamous duo, mostly in part to how irresistibly they pair with each other. The acidic, creamy soup against the crusty, rich sandwich—perfect foils of each other. In that way, the pair is quite sophisticated, yet after one dunk, you find yourself consumed and comforted in memories of childhood. Something so simple and familiar as tomato soup and a grilled cheese can be elevated to something the whole family can enjoy. Techniques can be perfected, palates can be challenged, yet nothing about it is threatening—it’s a one-way ticket to the perfect day in your most familiar place: home.
Serves 4 cups of comfort and 2 bangin’ sammies
For the Soup:
2 lbs assorted tomatoes (we use Roma, vine-ripe, and cherry tomatoes)
**The larger tomatoes are quartered, and the cherry tomatoes are kept whole
2 medium shallots, peeled and halved
2 cloves of garlic, smashed / peel on
2 tbs good quality olive oil
1 tbs balsamic vinegar (we use aged balsamic for that rich, sweet flavor—this product is more expensive, but totally worth it in many applications)
1/2 tsp dried basil
1/2 tsp salt
1/2 tsp black pepper
1 bay leaf
1/4 cup cream, optional (this soup is really good without it if you want to keep it vegan)
chiffonade basil, finishing oil, and cracked black pepper, for a garnish
For the Sandwich:
4 slices of bread (we use rye—there’s just something so f***ing good about it)
2 slices American cheese
4 slices Swiss cheese
2 tbs mayonnaise
4 tbs butter (1/2 a stick), room temperature
Preheat the oven to 375° F
Make the soup. Place the tomatoes, shallots, and garlic on a large sheet tray. Cover them with the oil, balsamic, dried basil, salt, and pepper and toss them until everything is evenly coated with the seasonings. Place the tray in the oven on the top rack, and roast for 30 minutes, or until everything has charred slightly.
Remove tray from oven, and let cool for a few minutes. Save 3 cherry tomatoes per person for a garnish later. Place all the remaining contents from the tray, including all the liquid that is at the bottom of the tray, into a blender. Blend on the highest setting until the soup is smooth. There still might be a few little bits here and there, but we like those. They make the soup feel homemade. Transfer the soup into a medium-sized pot. Add the bay leaf. Bring the soup up to a slight simmer, then reduce the temperature to the lowest setting on your stove, and cover. Allow it to stay warm on the stove until you’re ready to eat. Add the cream just before serving to avoid curdling the cream.
Make the grilled cheese. Butter one side of each slice of bread with 2 tbs of butter. Spread the mayonnaise evenly on the other side of each slice of bread. Distribute the cheeses evenly amongst the four slices of bread on top of the side with mayonnaise.
Heat a large skillet over medium heat. Melt 1 tbs of butter in the pan. Once melted, put the buttered side of the bread down in the skillet. At this point, there should be four slices of bread in the skillet, not two sandwiches. Watch the bread carefully, and when the bottom of the bread has become slightly golden, place two of the toasts on top of the other two to create two sandwiches. Add the last tbs of butter. Continue to cook the grilled cheeses, flipping frequently, until both sides of the sandwiches are beautifully golden brown, and the cheese is melty and perfect.
**Tip: Don’t make your skillet too hot. This could result in browned, toasty bread, and not-melty cheese. You want the cheese to have time to melt.
Serve the grilled cheese with a cup or bowl of tomato soup. Garnish the soup with a little cream, olive oil, the reserved cherry tomatoes, basil, and freshly cracked pepper if you desire. Cut the grilled cheese in half.
Dunk. Bite. Chew. Swallow. Moan. Sigh. Repeat.