Classic Comfort: Grilled Cheese and Tomato Soup

A bowl of tomato soup and a grilled cheese sandwich is one of the classic pairings of all time. It rates right up near the top of the comfort-food scale with meatloaf, mac ‘n’ cheese, mashed potatoes and ice cream.

It’s been a while since I’ve had some homemade tomato soup and a grilled cheese sandwich. As a kid, we could always count on a lunch featuring the pair at least once every week or so.

I’ve been thinking about that a lot lately. First, a friend, Pete Hougum, shared a recipe for tortellini, spinach and tomato soup that he said was simply delicious. I’d been meaning to make it but mislaid the recipe until last night.

Then, an email came my way from the Wisconsin Milk Marketing Board asking me to share with readers information about an upcoming contest for the top homemade grilled cheese sandwich in the country. Of course, contestants were asked that the recipe include some Wisconsin cheese.

The winner of the contest, which ends May 8, will receive an all-expense-paid trip for two to New York City and a host of other tasty prizes. Fifteen other winners will take home prizes including gift cards and Wisconsin Cheese baskets. (To enter and for more contest information, visit

Here’s a sample of a grilled cheese sandwich recipe from the WMMB, along with the tomato soup recipe I’m hoping to try.

The Dagwood
9 tablespoons butter, at room temperature, divided
1 red onion, sliced 1/8  thick
Salt and pepper
8 slices classic white bread
8 slices Wisconsin American cheese
4 slices Wisconsin Sliced Swiss
8 ounces smoked ham, sliced
2 large heirloom or beefsteak tomatoes, sliced ¼-inch thick (8 slices)
Heat saute pan over high heat. Add 1 tablespoon butter; melt and add onion slices. Add a pinch of salt and pepper; cook for 3 to 5 minutes. Remove to plate; reserve. Butter one side of each bread slice. Heat saute pan over medium heat. Add 4 bread slices, butter-side down. Layer on each slice of bread: 1 slice American cheese, 1 slice Swiss cheese, 2 ounces ham, about 1 tablespoon sauteed onions, 2 slices tomato and an additional slice of American cheese. Top sandwiches with remaining 4 slices bread, butter-side up. Saute sandwiches for 3 minutes: turn carefully, and grill until golden brown and the cheeses are melted.
Yield: Serves 4.

Tortellini, Spinach and Tomato Soup
2 tablespoons unsalted butter
6 to 8 cloves garlic
4 cups low-salt chicken broth
6 ounces fresh or frozen tortellini
14-ounce can diced tomatoes, with juice
10 ounces spinach, washed, stemmed, coarsely chopped
8 to 10 basil leaves
Parmesan cheese, grated
Melt butter in large saucepan over medium-high heat. Add garlic and saute until fragrant, about 2 minutes. Add broth and bring to a boil. Add tortellini and cook halfway, about 5 minutes for frozen pasta, less if using fresh. Add tomatoes and juice, reduce heat to simmer and cook just until pasta is tender. Stir in spinach and basil and cook until wilted, 1 to 2 minutes. Serve with grated Parmesan.