Ventimiglia attended El Modena High School in Orange, California, where he wrestled, acted in drama productions and served as student government president, graduating in 1995. At eighteen, Ventimiglia studied at the American Conservatory Theater for their summer program, subsequently attending the University of California, Los Angeles as a theatre major. At eighteen, Ventimiglia pursued an acting career, first starring as a gay teenager in "Must Be the Music", a short film released as part of Strand Releasing's "Boys Life 2". He enrolled at UCLA before landing a role on "The Fresh Prince of Bel Air," guest starring on television series including "", "Sabrina, the Teenage Witch", "" and "Boston Public." He played Jed Perry, in the short-lived Fox TV series, "Opposite Sex", which originally aired in 2000. From 2001 to 2006, Ventimiglia played brooding teen Jess Mariano on "Gilmore Girls"; he was introduced in the second season as a leading cast member. He signed on for a spin-off of "Gilmore Girls" called "Windward Circle" which was to be focused on the relationship between Jess and his estranged father (played by Rob Estes), but the proposed series never made it to air. Afterward, he dropped down to a guest star/recurring cast member, and he came back for four episodes in season four and two episodes in season six. In the third and final season of "American Dreams", Ventimiglia played Chris Pierce, the rebellious boyfriend of Meg Pryor (Brittany Snow); Pierce and his single mother, Shelly (Daphne Zuniga), a Playboy bunny, move into the house next to the Pryors. In 2005, he starred in the mid-season replacement series "The Bedford Diaries". The producers had only Ventimiglia in mind, but the show lasted only eight episodes and was one of several shows not picked up by the newly formed network The CW. In between television work, Ventimiglia had supporting roles in the horror films "Cursed" (2005), directed by Wes Craven, and "Stay Alive" (2006), as well as starring roles in the short-film "Intelligence" and the full-length feature "Dirty Deeds" (2005). The same year, he was cast as Robert "Rocky Jr." Balboa, the son of Rocky Balboa, in the sixth "Rocky" installment "Rocky Balboa" which was released in December 2006.