Prepare the asparagus by snapping off or cutting the woody ends of the stems. Place the asparagus on a sheet pan and drizzle with 1 tablespoon olive oil. Season with salt and pepper and toss.
Cook the asparagus in the oven for 20-25 minutes if thick, 17-20 minutes if thin.
Take the basil leaves and slice thinly.
Heat 2 tablespoon olive oil in a skillet over medium heat. Once hot, add the cherry tomatoes and season with salt and pepper. Cook 5-7 minutes until blistered, stirring frequently.
As tomatoes soften, smash a few carefully with a spoon to release the juices into the olive oil.
Remove asparagus from the oven when done. Plate, then spoon tomatoes and oil over the asparagus. Squeeze juice from half a lemon over the top. Add the sliced basil. Add salt and pepper.