Preheat the oven to 375 degrees F. Add the broccoli, oil, crushed red pepper, garlic and 2/3 cup water to a large skillet and stir until combined. Cover and bring to a boil. Let the broccoli steam until bright green and just crisp tender, about 3 minutes. Remove the lid and let the water continue to boil until it is completely evaporated, 3 to 4 minutes. Stir in 1/2 teaspoon salt and a few grinds of pepper and transfer to a medium bowl. Let cool slightly, about 15 minutes. Stir the cream cheese.
Coat the back of a baking sheet with cooking spray. Unroll both cans of crescent dough and separate unto 16 triangles. Put a 5-inch ramekin in the center of the prepared baking sheet. Arrange the triangles in a ring around the ramekin so the short sides of the dough are touching the ramekin, overlapping slightly, and the pointed ends are facing outward (it should look like a giant sun).
Spoon the broccoli mixture over the short ends of the triangles closest to the ramekin. Cover the broccoli with the cheese slices and remove the ramekin. Take hold of the pointed end of one of the triangles and fold it up and over the filling, tucking the tip under the bottom edge of dough to secure (the dough will not cover the filling completely). Repeat with the remaining triangles (there will be some gaps where you can see the broccoli mixture).
Bake until the dough is golden brown and the cheese is melted, about 25 minutes. Let cool for 15 minutes. Use a spatula to slide the ring off the baking sheet onto a platter. Serve with Ranch dressing for dipping.
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