Bossi trained, at the Brera Academy, with Giuliano Traballesi and Andrea Appiani, a friend with whom he later collaborated. In Rome between 1785 and 1801, he studied Michelangelo and began a long friendship with Canova. In 1802 Bossi travelled to Lyon, France, where he met Neoclassical painters such as Jacques-Louis David. In addition to being a designer and an academic painter, Bossi was an intellectual and a scholar. He played an important role in Napoleonic Milan. His Jacobin sympathies gained for him the position of secretary of the Brera. Because of Bossi's reforms, which formed the foundation of the Italian academic system, the Brera became the most prestigious academy in Italy. During his short life, Bossi wrote poetry, criticism and art history, and formed an important collection of old master drawings, as well as a rich library.