Work as a child actress
After appearing as herself in the direct-to-video of Disney Sing-Along Songs called Beach Party at Walt Disney World in 1995, Boorem had her first televised role in 1996 as a guest on the series Touched by an Angel. That was followed by a supporting part in The Education of Little Tree (1997), based on the controversial memoir of the same name by Forrest Carter. David Noh of Film Journal International deemed her performance as a young friend of the titular Cherokee character "delightful." For her performance, she was nominated for a Young Artist Award. The same year, Boorem had a guest role playing the young Ally McBeal in the 1997 pilot episode. She also had a supporting role in A Walton Easter, a television film spin-off from The Waltons, which aired in the spring of 1997. She subsequently had a supporting role in the Christmas film Jack Frost (1998) starring Michael Keaton, for which she was nominated for a YoungStar Award for Best Actress in a Drama Film.
She then had a part in Disney's live-action film Mighty Joe Young (1998), playing the young counterpart of Charlize Theron's character. She appeared on television again as a main cast member of the comedy series The Tom Show, which aired for one season between 1997 and 1998; in the series, she portrayed the daughter of a television producer, played by Tom Arnold. In late 1999, Boorem had a supporting role in the ensemble drama Things You Can Tell Just by Looking at Her, opposite Glenn Close and Cameron Diaz.
Also in 2000, Boorem had a central role in the Revolutionary War historical drama The Patriot (2000), playing the daughter of a soldier (portrayed by Mel Gibson). For her performance, she was nominated for her third Young Artist Award as part of an ensemble cast. She subsequently appeared opposite Morgan Freeman and Anton Yelchin in the thriller Along Came a Spider (2001), playing the kidnapped daughter of a United States Senator. The following year, she was again cast opposite Yelchin with a lead in the drama Hearts in Atlantis (2001), playing a young girl who has mysterious interactions with an elderly man (played by Anthony Hopkins) in her community. A supporting role in Penny Marshall's period drama Riding in Cars with Boys (2001) followed, and a part as the younger sister of Kate Bosworth in the surf film Blue Crush (2002). In 2003, she had a supporting role opposite Julia Stiles and Shirley MacLaine in the romantic comedy Carolina. Between 2002 and 2003, Boorem had a recurring guest role on the sixth season of the series Dawson's Creek, portraying Harley Hetson. For her role, she earned a Teen Choice Award nomination for Choice TV Sidekick.