In 2014, he starred as Josh Pfefferman in the Amazon Prime Original Comedy-Drama Series Transparent, alongside Jeffrey Tambor, Gaby Hoffmann, Amy Landecker and Judith Light. The series was met with widespread critical acclaim, earning 11 Primetime Emmy nominations, including nominations for Best Comedy Series and Best Actor in a Comedy Series for Jeffrey Tambor. In the second season of the show, Duplass' role became more prominent, and he was nominated for the Critics' Choice Television Award for Best Supporting Actor in a Comedy Series.