teenage girl who disguises herself as a boy to get the attention of her absent mother. Ian Somerhalder as Hamilton Fleming, a student at the school and the son of the dean. Hamilton finds himself confused by his attraction to Jake. Kate Bosworth as Bella Banks, Will's childhood friend – a pretty townie torn between Scout and fellow New Rawleyian, Sean. Ed Quinn as Finn, coach of the rowing team and also a teacher. Notable guest appearances Matt Czuchry as Sean McGrail, Will's long-time best friend and baseball teammate as well as a childhood friend of Bella's, he eventually becomes Bella's boyfriend. Deborah Hazlett as Susan Krudski, Will's mother. Works at a New Rawley beauty salon named "Glamorama". Charlie Hunnam as Gregor Ryder, bad-boy and student at Rawley Academy. Michelle Monaghan as Caroline Busse, Will's love interest. Cyndi Johnson as Paige Bennett, old friend of Scout's family. Kathleen Bridget Kelly as Kate Fleming, Hamilton's mother and the dean's wife. Gabrielle Christian as Grace, Bella's irresponsible sister. Beau Gravitte as Senator Calhoun, Scout's dad. Glynnis O'Connor as Donna Banks, Bella & Grace's mom. Naomi Kline as Lena, a student visiting Rawley Academy for girls showing a romantic interest in Jake. Production Steve Antin credits a stop at a New England gas station as the inspiration for the series. He was a little surprised to see four teenage girls working as pump jockeys. "One of them said, 'My dad owns the station.' I just thought this was the sweetest thing I ever saw." The pilot was filmed in Atlanta in 1999 and with a somewhat different cast. The character of Finn was played by Jeremy Sisto in the pilot, but between the pilot and the reshoots for the series, Sisto was cast in the title role of CBS' miniseries Jesus. When the production relocated they also replaced secondary roles, and the only original cast members that remained were the five principal actors. The pilot's soundtrack contained recognizable tracks by Fatboy Slim, New Radicals, and The Flys, but after the reshoots, Antin replaced them with favorites like Nick Drake's "Pink Moon" and Israel Kamakawiwo'ole's "Over the Rainbow", which at the same time became fashionable in commercials for Volkswagen's Cabrio convertible and eToys.com. A subplot in the pilot involving an affair between Finn and the dean's wife was dropped and later inserted into the third episode of the series. The series was filmed in