The San Antonio native moved to Los Angeles at 18 to take a crack at acting, and made an uncredited performance in the Lifetime sudser the same year, “A Little Inside” (1999). He starred in the passed-over pilot for “Silent Witness” (NBC, 2000) but quickly tapped for the role of Rory’s first flame on “Gilmore Girls” (WB, 2000-2004). He spent four years on The WB hit, but kept busy making movies, pilots and a short-lived show. After the failed pilot “Close to Home” (Fox, 2001) with Katharine Towne and Gabrielle Union, he appeared in the adaptation of Madeline L’Engle’s “A Ring of Endless Light” (Disney, 2002) with Mischa Barton and James Whitmore. In 2003, Padalecki played the title role in the WB’s “Young MacGyver” with Ron Canada. As the nephew of the better-known MacGyver, Padalecki joined the Phoenix Foundation after leaving school and found himself easily fitting into his uncle’s shoes. However, this series, too, did not ultimately make The WB's fall schedule.

Padalecki later made another uncredited performance, this time as a high school heckler of “Smallville” star Tom Welling in the feature comedy “Cheaper By the Dozen” (2003) with Steve Martin, Piper Perabo and Hilary Duff. He also lent his name to the disastrous Olsen twins vehicle “New York Minute” (2004). The angel-faced actor’s first big shot came with a role in the update of of the 1965 Jimmy Stewart adventure drama “Flight of the Phoenix.”. The 2004 version boasted a star-studded cast pairing Padalecki with the likes of Dennis Quaid, Giovanni Ribisi, Tyrese Gibson and Hugh Laurie. The movie, however, was widely panned as dramatically inferior to the original and was widely ignored. The reviews didn’t get much better as Padalecki marked the beginning of his post-Gilmore years with soapy gore. He starred in “House of Wax” (2005) with young heartthrobs Elisha Cuthbert and Chad Michael Murray, but the initial media interest in the film centered around the cinematic debut of notorious heiress Paris Hilton. Once the film was screened, interest faded altogether.

Padalecki returned to The WB to star in “Supernatural” (2005 - ), fittingly slated to follow “Gilmore Girls.” Still wearing floppy, haphazardly shorn locks, he won the heart of many a young WB fan opposite Jensen Ackles as a pair of brothers who delve into the paranomal searching for their missing father and tying to solve the mystery of their mother's death. His next role was in “Cry_Wolf” with Jon Bon Jovi as part of a group of prep school students whose game of spreading lies causes no one to believe them when they a genuine serial killer stalks them. The film was oderately well-received amid a slew of inadequate slashers and ill-conceived sequels.