Start a pot of pasta water in a large pot. Add enough salt the water tastes salty.
Heat the large skillet or everyday pan over medium heat. Once hot, add 1 tablespoon of the olive oil, followed by the shallot. Cook the shallot until soft and translucent.
Add the tomatoes to the pan. Give the tomatoes a quick stir in the olive oil, then let them sit for about 30 seconds. The tomatoes will begin to blister and burst.
When the tomatoes start to burst, turn the heat down to medium-low and add the garlic, cook until fragrant. Use the back of the wooden spoon to press on the tomatoes help release their juices into the pan. As the juices release, the brown caramelized bits at the bottom of the pan will soften, use the back of the wooden spoon to scrape them up. Continue until all tomatoes have burst.
Add the pasta to the boiling water and cook 1 minute less than package instructions.
Add the remaining tablespoon of olive oil, oregano and crushed red pepper flake (optional) to the tomatoes and continue to stir scraping any caramelization off the bottom of the pan.
Just before the pasta is finished cooking, take a ladle of the hot pasta water and add it to the tomatoes. Stir to combine, again scraping any caramelized bits from the bottom of the pan.. Strain the pasta, reserving the pasta water. You'll want the hot pasta water close to your skillet with a ladle.
Taste the sauce, adjust for seasoning with salt and black pepper to your tastes.
Add the drained pasta to the tomatoes and stir well to coat the pasta with the sauce. Stir in ½ the basil. Add the parmesan cheese and continue to stir. If the sauce seems dry, add more pasta water, ¼ cup at a time.
Serve immediately topped with more parmesan cheese and the remaining basil.