Montella's nickname during his playing career was "Aeroplanino", in reference to his small stature and trademark goal celebration, in which he spread his arms like wings. A prolific goalscorer, throughout his playing career Montella played as a forward for Italian clubs Empoli, Genoa, Sampdoria and Roma, and also had a spell on loan in England with Fulham. He is mostly remembered for his performances with Roma (1999–2007), where he won the Serie A title and the Supercoppa Italiana during the 2000–01 season, also later reaching the 2003 Coppa Italia final with the club. In 2013, Montella was inducted into the A.S. Roma Hall of Fame. At international level, he made 20 appearances for Italy between 1999 and 2005, scoring three goals; he was notably a member of the Italian team that reached the final of UEFA Euro 2000, and he also represented his country at the 2002 FIFA World Cup.