Combine the tomatoes, salt, pepper, sugar, and garlic in a large bowl and stir to combine. Set aside.
Add three tablespoons of olive oil to a large skillet over medium heat. When the oil is hot, add the bread cubes and toss to coat with oil. Toast the bread cubes, frequently stirring for five minutes, or until the bread is golden brown.
Add the tomato mixture to the bread cubes and stir to combine. Cook the tomato mixture for five minutes, or until the tomatoes are bubbly. Remove the pan from the heat and add the basil. Stir to combine.
Spread the tomato mixture evenly in a medium-size baking dish, which has been sprayed with no-stick cooking spray. Top with the parmesan cheese and drizzle two tablespoons of olive oil evenly over the casserole.
Bake for 35 minutes, or until the cheese is browned and the tomatoes are bubbly. Serve immediately.
Notes
I added a layer of thinly sliced tomatoes over the top of the casserole in the photos so it would look better in photographs. This is an optional step, and you can add them or leave them off.I think meaty Roma or Italian Pulm tomatoes work best in this casserole, but you can use whatever you have on hand as well as a variety. Roma's are denser, have a thicker fruit wall, and fewer seeds and pulp than most other tomatoes. If you use anything other than Roma or cherry tomatoes, be sure to squeeze out any excess pulp and seeds before adding them to the dish. Fresh basil is best, but In a pinch, you can use dried basil instead. If you use dried because the flavor is much more concentrated, and you only need to add one tablespoon. If you want to change things up a bit, feel free to add a handful of panko bread crumbs to the parmesan cheese topping. This is a great make-ahead dish. It can be assembled a few hours ahead and then baked right before you are ready to serve it.