Grilled Cheese Sandwich with Eggplant and Tomatoes

Joan Nathan


"What's more American than a grilled cheese sandwich? I like mine fried in a frying pan and weighted down so the bread is browned and the cheese oozes out."

Buy Joan Nathan's JBF Award–winning cookbook, The New American Cooking, from our Amazon store.


4 sandwiches


  • 3/4 cup vegetable oil 
  • 1 teaspoon salt
  • 1/2 teaspoon black pepper 
  • 1 garlic clove, minced 
  • 1 medium eggplant (about 1 pound) cut in 1/2-inch-thick rounds
  • 1 tomato, sliced, or 1 cup sun-dried tomatoes in olive oil, drained
  • 8 thick slices of Vermont cheddar cheese 
  • 8 slices of whole-wheat bread
  • 2 tablespoons butter


Preheat the broiler and set the rack 4 inches below the top. Cover a baking sheet with aluminum foil. 

Mix the oil with the salt, pepper, and garlic in a small bowl. Dip the eggplant slices in the oil, shaking to get rid of any excess oil, and place on the baking sheet. Place under the broiler for 5 minutes or until the eggplant is golden. Flip the eggplant over, continue cooking until golden, remove, and cook on the cookie sheet. 

Place the eggplant and the tomatoes in a medium mixing bowl. Don’t worry about the excess oil. 

When ready to make the sandwiches, place a piece of cheese on each slice of bread, and add about 1/4 cup of the eggplant and tomatoes on each of the 4 slices. Top with the other 4 bread slices. 

Melt butter in a skillet or griddle over medium heat and grill the sandwiches a few minutes on each side, until the crust is crisp, golden brown.