In a large pot of boiling water, cook the penne according to package instructions until al dente, about 13 minutes. Meanwhile, in a large skillet, heat the olive oil over medium heat. Add the garlic, and cook, stirring until just golden brown, about 1 minute. Add the cherry tomatoes, oregano, crushed red pepper, 1/2 tsp. salt and 1/4 tsp. pepper. Reduce the heat to low and cook, stirring, until tomato juices run, about 3 minutes. Add the penne, olives, parsley, and 1/4 cup Parmesan to the skillet and toss to combine. Serve with more cheese if desired.