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For the asparagus, preheat the oven to 400 degrees F. Snap the tough lower ends off the asparagus and discard them. Cut the asparagus spears into 1-inch pieces.
Place the asparagus on a large, rimmed baking sheet and toss with the olive oil, salt and pepper. Roast until tender, about 10 minutes. Remove from the oven and set aside.
For the balsamic butter, add the vinegar to a small saucepan. Simmer over medium heat until the vinegar is reduced to about 3 tablespoons, about 5-10 minutes.
Stir in the brown sugar, pepper and salt. Remove from the heat.
For the pasta, cook the penne in a large pot of lightly salted boiling water until al dente (or desired tenderness). Drain the pasta and return to the pot.
Add the butter and toss with the pasta until the butter is melted and the pasta is evenly coated.
Add the vinegar reduction to the pasta. Toss to combine well. Add the asparagus and Parmesan; toss. Season to taste with additional salt and pepper, if needed.
Serve warm or at room temperature with extra Parmesan cheese, for serving, if desired.