Massimo Cavalletti was born in Lucca, where he began his vocal studies with Graziano Polidori before attending the Academy of La Scala in Milan, where he refined his vocal technique with Luciana Serra. In October 2004 he made his operatic debut at the Teatro Donizetti of Bergamo in Parisina in a production of the Academy of the Teatro alla Scala. In 2005, still a student of the Academy, he made his debut at La Scala, where since then he has starred in over 100 performances and over 10 different roles.

Massimo Cavalletti has worked with such conductors as Daniel Barenboim, Zubin Mehta, Riccardo Chailly, Nello Santi, Fabio Luisi, Daniele Gatti, and Daniel Harding.

His DVD/Blu-Ray recordings include La bohème from Salzburg, Turin and Valencia, Falstaff from Zurich and the Salzburg Festival, and Simon Boccanegra from La Scala.