Ballerini was born to an Italian father, the poet Luigi Ballerini, and an American mother, the photo historian and writer Julia Ballerini. He grew up between New York City and Milan, Italy. He is a dual citizen, and bilingual. His early schooling took place in New York, at P.S. 41 and later Friends Seminary, before he left home at age 14 after his parents' divorce for boarding school at Deerfield Academy. From there, he attended Wesleyan University, graduating a Bachelor of Arts degree English after studying under Paul Horgan. The summer following his graduation, Ballerini was given a scholarship to study Latin in Rome with Father Reginald Foster, a Vatican priest. While in Italy, Ballerini discovered a group of international actors who were forming a theater company. He quit his studies and joined the troupe. The following fall, he attended regular acting classes in New York at HB Studio and the Lee Strasberg Theatre and Film Institute. He was then invited to became an observer at the Actors Studio.
Ballerini's first professional role on screen was as an autistic teenager on Law & Order (1995). Following that he had small roles in I Shot Andy Warhol (1996) and The Pallbearer (1996), opposite David Schwimmer. In 1997 he starred in the John Leguizamo comedy The Pest (1997) before appearing in Whit Stillman's The Last Days of Disco (1998) and Amos Kollek's Sue (1998), then again in starring roles in Martin Davidson's Looking for an Echo (2000) and the action blockbuster Romeo Must Die (2000).
That same year Ballerini was cast as the "star chef" in Bob Giraldi's Dinner Rush (2001) opposite Danny Aiello. The film grossed only $638,227 but received largely positive reviews.

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