Combine popcorn and 1/4 cup olive oil in a 2-quart saucepan; cover. Cook over high heat, continuously shaking the pan, until the popcorn is popped and the lid begins to lift from the popcorn, about 5 minutes. Pour popcorn into a large bowl.
Mix 2 tablespoons olive oil, Italian seasoning, and garlic salt into popcorn; toss to coat. Add Parmesan cheese and mix well.
