Warm 1/4 cup olive oil in a large skillet over medium heat. Add 4 thinly sliced garlic cloves and saute for 30 seconds.
Add 1 pound cherry tomatoes, 1/2 teaspoon kosher salt, and 1/4 teaspoon black pepper and simmer for 20 minutes, stirring occasionally, until the tomatoes are beginning to burst.
Meanwhile, bring a pot of heavily salted water to a boil and cook 8 ounces ravioli for 3 minutes when the tomatoes are looking near-ready. DO NOT DRAIN THE WATER, YOU NEED IT FOR YOUR SAUCE!
Smash most of the tomatoes gently with a wooden spoon or spatula. Remove skillet from heat.
Add the cooked ravioli, 1/4 cup pasta cooking water, and 1/4 cup parmesan cheese to the tomato mixture and toss to combine until a silky sauce coats the ravioli.
Add in 1/4 cup torn basil and toss to combine.Serve immediately, garnished with more basil and parmesan.