Leopardi has been in films since he was 5, and is known for his role at eleven years old as Michael "Squints" Palledorous in the 1993 film The Sandlot. Leopardi also made a single appearance in Boy Meets World, in the pilot episode. He also appeared in runs as bully Alan White on the short-lived NBC series Freaks and Geeks and as the geeky Navy Sailor, Kyle, on The CW network's Gilmore Girls. He has appeared in various other films and television series, including the 1995 comedy Houseguest. In 2007, he reprised his role of Michael 'Squints' Palledorous in the third installment of The Sandlot series, fourteen years after the original movie. During the late 1990s, he played a recurring role as Otto the Nome Prince in the ABC cartoon series The Oz Kids.
