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Preheat oven to 450 degrees. Meanwhile, trim ends from broccoli rabe and thinly slice garlic cloves. In medium bowl, toss broccoli rabe and garlic with olive oil, 1 tablespoon balsamic vinegar, sea salt, and freshly ground pepper.
Place on large, rimmed baking sheet and roast 8-10 minutes, until crisp-tender with leaves slightly charred. Drizzle with rest of balsamic vinegar and sprinkle of red pepper flakes, grated cheese, and toasted nuts before serving.