In The Carrie Diaries, the forthcoming prequel to the hit series Sex and the City, set to air on The CW this winter, 21-year-old Austin Butler plays beleaguered quasi-love interest to a teenage Carrie Bradshaw, whom we meet during her junior year in high school in a bucolic Connecticut town. However, the show—which, like SATC, is based on the writings (and, in parts, the life) of author Candace Bushnell—quickly flashes forward to the streets of neon-lit, early-1980s Manhattan after Carrie (played in her younger incarnation by Annasophia Robb) lands an internship at a law firm, and life and love in the Big Apple predictably begin to spin out of control. Butler's character, Sebastian, is a neglected rich kid-cum-high-school-rebel whose uneasy relationship with Carrie presages some of the romantic complications that we all know she will come to experience (and obsess over) later in life. Nevertheless, Butler manages to spike Sebastian's requisite tough-guy cool with a little bit of adolescent insecurity. "He likes the mystery," explains the actor, who grew up between Anaheim, California, and Arizona, and has previously had small parts on Zoey 101, CSI: NY, and Hannah Montana. "Sebastian has gotten kicked out of multiple schools, there are rumors that he's selling drugs and he doesn't deny them." Inevitably, Sebastian's feelings for the young Carrie stir up all kinds of teenage angst. But for Butler, perhaps the most intriguing aspect of working on The Carrie Diaries has been the fact that the show is set nearly a decade before he was born. How did he prepare? By stocking up on John Hughes films and quickly becoming a Breakfast Club (1985) disciple-even going so far as to draw upon Judd Nelson's infamous bad-boy-with-a-heart, John Bender, a touch point for Sebastian. And yes, he also screened episodes of the original Sex and the City series. "I never pictured myself on Sex and the City," he says. "But I watched the first two seasons in under a week and . . . Well, I get why women love it."