Paper Plane
Invented by Sam Ross at Milk & Honey in New York City around 2007, the Paper Plane is a modern classic built entirely on equal parts — bourbon, Aperol, Amaro Nonino, and fresh lemon juice. It sounds like it shouldn't work, but the interplay between the sweetness of bourbon, the bitter orange of Aperol, the herbal complexity of Nonino, and the citrus lift of lemon is absolutely masterful. Use Bulleit or Wild Turkey 101.