In 1996, following an appearance in Romeo and Juliet, twenty-year-old Bolle was promoted to principal dancer at La Scala. He left that position when he was 21 to pursue a freelance career. Since then he has starred in many ballets including Sleeping Beauty, Swan Lake, Cinderella, The Nutcracker, Giselle, La Esmeralda, and In the Middle, Somewhat Elevated.