The same year Ventimiglia played a soccer player in the teen classic “She’s All That” (1999) with Freddie Prinze, Jr., Rachel Leigh Cook, Anna Paquin, Gabrielle Union and Dule Hill, Kieran Culkin and Lil’ Kim. Prinze pretended to be in love with the awkward, bookish Cook and has actually fallen for her when she discovers that his affections started as a joke. In "Speedway Junky" (1999), Ventimiglia was cast with Jesse Bradford, Darryl Hannah, Tiffani Thiessen, Patsy Kensit and Warren G. Bradford turned in a much-lauded performance of a high school boy who runs away from his home to realize his dream of becoming a race car driver.

All of this supporting experience was enough to land the actor a starring role in “Opposite Sex” (Fox, 2000) with Garcelle Beauvais. Ventimiglia played a hormonal 15-year-old boy who moves to Northern California with his recently widowed father and finds himself as one of three boys in a previously all-girls high school. He followed the short-lived drama with “Massholes” (MAX, 2000), a largely ignored telepic about four young men facing consequences and important life decisions that will affect them forever. The actor then co-starred in another growing pains flick, “Nice Guys Finish Last” (2001), a short about a sweet high school boy facing de-virginization. Also in 2001, Ventimiglia snagged a coveted guest spot on “CSI: Crime Scene Investigation” (CBS) playing a murderer.

Already a seasoned veteran at 24, Ventimiglia was cast in the role that would make him famous, playing brooding love interest of Rory (Alexis Bledel) on the WB’s “Gilmore Girls” (2001- ). The chemistry Ventimiglia and Bledel expressed on the show carried over when the two actors engaged in an off-screen romance. For many viewers, Ventimiglia’s Jess was a refreshingly realistic character on a supremely stylized show. His unexpected disappearance cast a shadow for more than a season. The absence was planned to facilitate his own “Gilmore” spin-off “Windward Circle” (WB, 2003) in which the troubled character would try to establish a relationship with his father. The show was cancelled after a 6-episode order with the official reason of high filming costs in Venice, CA, but lack of interest from viewers must also have been a factor. Ventimiglia bounced back quickly with a three-episode stand on “Boston Public” (FOX, 2003) and a starring role in “Winter Break” (2003) with George Lazenby and Anna Farris. He played a recent college grad who passes up a steady job in upstate New York to screw around in a skiing community.

He had two big guest spots in 2004, dropping into “Law & Order: Special Victims Unit” (NBC) and “Gilmore” to confuse old flame Rory and lecture his uncle and former caretaker Luke about his life decisions. The same season, Ventimiglia was a recurring character on “American Dreams” (NBC, 2004). His character Chris Pierce was written for him after he met the show’s creators. In 12 episodes, his character was a terrible influence on the otherwise well-behaved young ladies.

Ventimiglia had a small role in Wes Craven’s “Cursed” (2005) with Christina Ricci, Shannon Elizabeth and Jesse Eisenberg. The vampire movie was recut, recast and reshot before making its way into theaters, but was still widely panned. Venitmiglia also starred in this disastrous “Dirty Deeds” (2005) in which a high school student tries to complete ten pranks—or dirty deeds—in one day. He made another stop in Star’s Hollow during the sixth season of “Gilmore” (2005) to talk some sense into Rory when no one else could get through. He was repaid for his loyalty to the WB with a 2006 mid-season replacement series also starring Matthew Modine. Set in a New York City liberal arts college, the ensemble drama focuses on sex and commuting

Ventimiglia next landed a regular role on the uninspired and ultimately short-lived “Bedford Diaries” (WB, 2005-06), a soapy drama set on the campus of a small liberal arts college that looked at the lives of a group of human behavior students who speak openly about their sex lives as a means of engaging in larger-than-life experiences. Ventimiglia played the school’s newspaper editor who threatens to expose an illicit affair between a student (Tiffany Dupont) and her professor. His next series, “Heroes” (NBC, 2006- ), was not only a hit, it became a cultural phenomenon. A comic book-like drama about eleven supposedly ordinary people from around the world who begin to discover they have supernatural powers, “Heroes” survived the cancellation onslaught of 2006 to rise above the competition and become one of the few new shows introduced that fall to be picked up for a second season. Ventimiglia starred as Peter Petrelli, a New York hospice worker who at first discovers that he can fly, but learns that he actually absorbs the superpowers of those around him. Meanwhile, the actor costarred opposite Sylvester Stallone in “Rocky Balboa” (2006), playing the Italian Stallion’s son struggling to get out from under the shadow of his father’s past.