After completing high school and her freshman year as a film major at New York University, Bledel was cast as sixteen-year-old Rory on "Gilmore Girls", more than capably handling the assignment of playing the daughter of a somewhat flaky but hardworking single mother (Lauren Graham). A straight-A student who jumps from her comfortable local public school to a high-pressure tony preparatory academy, Rory faces the challenges of any high schooler, including peer pressure, young love and seemingly hopeless awkwardness. Bledel's excellent chemistry with TV mom Graham and her (often heartbreakingly) realistic portrayal of the character coupled with the poignant and fresh writing of the series itself led to "Gilmore Girls" critical acclaim and cult following, holding its own as a portrait of a common family unit under-represented in popular culture despite a deathly time slot that had it competing with "Survivor" and "Friends" in its first season. While the show wasn't so much a breakout hit as a heart-tugging sleeper with good potential, Bledel seemed poised to go far, both within the series and in other projects. The actress lensed her first feature film role in "Tuck Everlasting," an adaptation of the popular children's novel by Natalie Babbit. Bledel's ethereal girl-woman quality (she played 15-year-old heroine Winnie while in her early 20s) earned her the role instantly--she was the first and only actress interviewed by director Jay Russell.

After a small turn as Martin Henderson's sister in the well-received Bollywood-meets-Hollywood musical "Bride and Prejudice" (2004), Bledel nabbed the pivotal supporting role of the blue-eyed hooker Becky in director Robert Rodriguez and writer-artist Frank Miller's visually arresting adaptation of Miller's crime noir comic book series "Sin City" (2005), appearing in the sequence "The Big Fat Kill" as well as the original coda for the film. That same year she was one of "The Sisterhood of the Traveling Pants" (2005), playing Lena, off to visit her salt-of-the-earth grandparents and other relatives on a Greek island, where she falls in love with a local boy.