Save to Pinterest The smell of slow-roasting tomatoes filled my tiny apartment kitchen on a rainy Sunday, and I knew I was onto something special. I had intended to make tomato soup, but the oven-roasted slices looked too good to blend into anything. A leftover heel of sourdough sat on the counter, and suddenly comfort food destiny took over.
My roommate wandered in, drawn by the caramelized tomato scent, and watched me assemble the first sandwich. When that first bite happened—crunch giving way to gooey cheese and intense tomato flavor—we both went quiet. Sometimes the simplest combinations are the ones that stop you in your tracks.
Ingredients
- 2 large ripe tomatoes: Look for tomatoes that give slightly when pressed and feel heavy for their size
- 1 tbsp olive oil: This helps the tomatoes roast evenly and develop those caramelized edges
- 1/4 tsp sea salt: Enhances natural sweetness as the tomatoes concentrate
- 1/4 tsp freshly ground black pepper: Adds just enough bite to cut through rich cheese
- 1/4 tsp dried oregano: Brings an Italian accent that bridges tomato and basil
- 4 slices rustic sourdough: Sturdy enough to hold everything together without getting soggy
- 2 tbsp unsalted butter: Use softened butter for even spreading and golden results
- 2 tbsp basil pesto: Homemade is wonderful but a good jarred pesto works perfectly here
- 4 slices mozzarella cheese: Provides that incredible stretch factor
- 4 slices sharp cheddar cheese: Adds the bold flavor punch mozzarella lacks
- Optional handful of baby spinach or arugula: Adds fresh contrast and a slight peppery note
Instructions
- Roast the tomatoes low and slow:
- Preheat your oven to 300°F and line a baking sheet with parchment. Arrange tomato slices in a single layer and drizzle with olive oil, then sprinkle with salt, pepper, and oregano. Roast for 50 to 60 minutes, flipping halfway through, until theyre deeply caramelized and concentrated but still intact.
- Prep your bread canvas:
- Spread softened butter on one side of each bread slice—think of it as creating your golden crust foundation. Lay two slices butter side down and spread the unbuttered sides with pesto, leaving a small border around the edges.
- Build your cheese tower:
- Layer mozzarella first, then arrange those gorgeous roasted tomatoes, followed by sharp cheddar. Add spinach or arugula if you want something fresh and green in the mix. Top with remaining bread slices, buttered side facing up like a shiny promise.
- Grill to golden perfection:
- Heat a skillet over medium-low heat and add your sandwiches. Let them cook for 4 to 5 minutes per side, pressing gently with your spatula. Flip when the bottom is deep golden brown and the cheese has started its melty journey.
- Let them rest before slicing:
- Give the sandwiches about two minutes on a cutting board so the cheese sets slightly. Slice diagonally and serve while still hot enough to make cheese strings when you pull apart the halves.
Save to Pinterest This sandwich became my go-to comfort food during grad school, especially during those long winter nights when the library kept me far past dinner. Something about the combination of warm bread and slow-roasted tomatoes felt like a hug from someone who knew exactly what I needed.
Getting the Perfect Cheese Pull
The secret to that dramatic cheese string is letting your sandwiches rest for a couple minutes after cooking. Cutting too soon sends all the gooey goodness running onto your plate instead of staying where it belongs. Patience pays off in both texture and presentation.
Making It Your Own
Sometimes I swap in sun-dried tomato pesto for double tomato intensity, or add a thin layer of fig jam if I want something sweet and savory. Gruère or smoked gouda bring completely different personalities to the party. The structure stays the same while the variations keep things interesting.
What to Serve Alongside
A crisp green salad with vinaigrette cuts through all that richness beautifully. Or go full comfort mode with a cup of tomato soup for dipping. Honestly though, this sandwich is substantial enough to stand alone with just some pickles on the side.
- A glass of crisp white wine like Sauvignon Blanc balances the buttery bread
- Save any extra roasted tomatoes for morning eggs or pasta later in the week
- This recipe doubles easily for a crowd—just use two skillets or work in batches
Save to Pinterest Hope this sandwich brings you as much comfort as its brought me over the years.
Common Recipe Questions
- → How do you prepare the tomatoes for this dish?
Slice ripe tomatoes about a quarter inch thick, drizzle with olive oil, sprinkle with sea salt, pepper, and oregano, then roast at 300°F for 50-60 minutes until deeply caramelized but still holding shape.
- → What type of bread works best?
Rustic sourdough or country-style bread is ideal for its sturdy texture that crisps well and holds the fillings without sogginess.
- → Can I use different cheeses?
Yes, mozzarella and cheddar provide a nice melt and sharpness, but provolone, fontina, smoked gouda, or gruyère can be delicious alternatives for varied flavor profiles.
- → Is there a way to add more greens to this dish?
Yes, adding a handful of fresh baby spinach or arugula inside the sandwich adds a fresh, peppery bite that balances the richness.
- → How do you cook the sandwich to get the perfect melt and crust?
Cook the assembled sandwich in a medium-low skillet or griddle, pressing lightly, for about 4-5 minutes per side until the bread is golden brown and cheeses have fully melted.
- → Are there suggested pairings with this meal?
This sandwich pairs wonderfully with a crisp green salad or a warm cup of tomato soup, enhancing the overall comforting experience.