In a medium skillet, heat the olive oil over medium heat. Once heated, add the cherry tomatoes. Cook for 1-2 minutes, then add then garlic, oregano, red pepper flakes, and basil.
Reduce heat to medium-low and cook until tomatoes are blistered, stirring occasionally. This will take about 7-10 minutes.
While tomatoes are cooking, cook the pasta in a large pot until soft. Drain.
Into the pasta pot, drain the cooked olive oil and herbs. Stir until pasta is coated. Add more olive oil if needed. Add salt and pepper.
Plate, then top with the cooked tomatoes and top with the parmesan and extra basil leaves, if desired.