Bring a medium pot of water to a boil. Generously salt the water, then add the orzo. Cook, stirring frequently, for 7–8 minutes or until al dente (for a slightly firmer bite, start tasting at 5 minutes).
Reserve 2 tablespoons pasta water, then drain the orzo and toss with 1 tablespoon olive oil to prevent sticking.
Heat the remaining olive oil in a large skillet over medium heat. Add the crushed garlic and halved cherry tomatoes. Cook, stirring frequently, until the tomatoes soften and begin to release their juices and the garlic is fragrant but not browned, about 5 minutes.
Remove skillet from heat. Stir in the Parmesan cheese and reserved pasta water a little at a time, mixing until the cheese melts and a light sauce forms. Add torn basil, salt, and pepper to taste.
Add the cooked orzo to the skillet and toss gently until well combined.
Serve immediately, topped with extra basil and Parmesan as desired.