Add balsamic vinegar and brown sugar to a large sauce pan over medium heat. Once it starts to bubble, reduce the heat to let it gently simmer, slowly stirring with a spatula.
Cook until it reduces by about half and starts to thicken. Let it cool for a few minutes. It should be a syrup consistency that will coat the back of a spoon. If not you can reheat and simmer a bit longer. Remove from heat and set aside.
Bake The Vegetables
Preheat oven to 400°F. Line a baking sheet with parchment paper. Set aside.
Prep the vegetable ingredients. Wash the tomatoes and asparagus and pat dry with a towel. Slice the cherry tomatoes in half. Snap the thick ends off of each of the asparagus. Roll the basil leaves together into a long tube, then slice thin strips from it.
Add 1 lb asparagus to a large bowl along with 1 tablespoon olive oil, ½ teaspoon salt, and ¼ teaspoon ground black pepper. Toss together.
In a separate bowl, add 1 pint sliced cherry tomatoes and mix with 3 minced garlic cloves, ½ teaspoon olive oil, ¼ teaspoon salt and ⅛ teaspoon ground black pepper. Toss together.
Assemble
Arrange the asparagus on half of the baking sheet. Add the tomatoes to the other half.
Bake for 10-12 minutes. Halfway through (after 5 minutes) remove the baking sheet and sprinkle the ½ cup parmesan cheese over top of the asparagus. Add back to oven and bake for last 5 minutes. The asparagus should be crisp tender when poked with a fork and the cheese with be melted. If not, bake an additional 1-2 mins.
Arrange the asparagus onto a serving plate in a diagonal row (see picture above). Top with the cherry tomatoes, then the fresh basil. Lastly, drizzle the balsamic reduction over top of everything. Now it’s ready to serve