Step 1: Preheat broiler with oven rack 8 inches from heat. Heat a cast-iron pan over medium , brush with oil. Place 1 tortilla in pan. Spread 1 1/2 tablespoon of pizza sauce on tortilla. Scatter 1/2 cup pepper Jack cheese over sauce and top with remaining tortilla. Cook until crisp and lightly browned on bottom, about 3 minutes. Flip quesadilla. Spread remaining pizza sauce evenly over quesadilla, and sprinkle evenly with remaining pepper Jack cheese. Arrange pepperoni slices evenly over quesadilla.
Step 2: Transfer quesadilla to a rimmed baking sheet. Broil in preheated oven until cheese is melted and pepperoni is slightly curled, 1 to 2 minutes.
Step 3: Slice quesadilla into 4 wedges. Serve with Parmesan, oregano, and crushed red pepper.
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