Holland grew up with two sisters: Brianna Holland and Piper De Palma, from mother Darnell Gregorio's then-marriage to film director Brian De Palma.[2] Holland attended Palisades Charter High School for only six weeks because her career was taking off and school peers were dismissive of her acting pursuits.[3]
In 1999, De Palma took Holland to a theatrical talent agency.[7] Since then, she has appeared in many national commercials. In 2001, when Holland was ten, she worked alongside her 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 initially played the role of Kaitlin Cooper on The O.C.,[7] replacing Shailene Woodley, as a recurring character in season 3, and then as a regular in season four.[9]
In December 2007, Holland was cast in the independent drama film Garden Party, playing the role of April, a troubled teenage aspiring model who tries to make it in Los Angeles. In September 2008, The CW announced Holland would appear in three episodes of the second season of the teen-drama television series Gossip Girl, created by The O.C. creator Josh Schwartz. Holland played the role of a rebellious 16-year-old model[7] who befriends and creates havoc for Jenny Humphrey (Taylor Momsen). In March 2010, Holland made a one-off return in the 16th episode of the third season, "The Empire Strikes Jack".
^Clarke, Cath (January 8, 2009). "First sight: Willa Holland". The Guardian. She was discovered by Steven Spielberg — in his garden no less...she was seven years old at the time, playing with his kids. Her stepdad is Brian de Palma.
^DeBruge, Peter (October 2, 2008). "Willa Holland: Discovered by Spielberg". Variety. "I was playing over at Steven Spielberg's house' – next door to stepfather Brian De Palma's place in the Hamptons – 'and he was filming little wedding scenes and doing homevideos,' she says. When her parents came to pick her up, Spielberg insisted, 'You've got to put her in front of a camera.' De Palma was for it, too.
^Weintraub, Steve (December 14, 2009). "First 'Legion' Clip". Collider.com. Archived from the original on February 7, 2015. Retrieved February 7, 2015.