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Holland spent the summer of 1999 in The Hamptons with her family. After a day playing at Steven Spielberg's home, the seed was planted that she should spend her life acting in film. Spielberg told her mother "You've got to put her in front of a camera!". The following year, 1999, De Palma took Willa to a theatrical talent agency. Since then she has shot many national commercials. During 2001 when Willa was ten, she worked alongside her cinematographer father in Ordinary Madness. She was even slated to co-star in the 2005 FOX series The Inside with fellow model Rachel Nichols, but left the show when writer Tim Minear was brought in to overhaul it. She played the role of Kaitlin Cooper on The O.C. for its third and fourth seasons. Incidentally, Willa Holland was a fan of The O.C. before landing the role of Kaitlin Cooper, Marissa Cooper's (Mischa Barton) rebellious "little" sister.[2][6][7] She was a regular on the entire fourth season. Willa currently attends private acting classes with one of LAs most esteemed acting coaches. She has recently graced the cover of Teen Vogue and Fashion 18 and has been featured in CosmoGirl!, as well as representing LeSportsac Fall and Winter 2006 The O.C. handbags for Macy's. She topped the High Critic's Top 20 lists for 2007 and 2008. Willa played a confused teenager (April) in the film Garden Party, which opened July 11, 2008 in Los Angeles, New York, Portland, and Seattle.[8] On September 5 2008 it was announced that Gossip Girl creator Josh Schwartz was giving her an at-least-3-episode stint in Season 2 of Gossip Girl in which Holland will play Agnes, a 16-year-old model working for Eleanor Waldorf. She is to create havoc with Taylor Momsen's character Jenny Humphrey.

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