Following her stunning debut, Lynskey floundered temporarily in Hollywood, but after playing a small role in Jackson's "The Frighteners" (1996), she garnered good notices as the "chubby" stepsister in "Ever After: A Cinderella Story" (1998), starring Drew Barrymore, and has worked steadily since. She portrayed a Cleveland girl who does the nasty in a church confessional en route to a KISS reunion show in "Detroit Rock City" and essayed her second starring role in "Foreign Correspondents" (both 1999). For the latter, in a part reminiscent of Pauline, she was a lonely young woman who starts to lose her grip on the real world when she begins receiving romantic postcards intended for someone else. Wil Wheaton played the well-meaning neighbor who tries to court her and bring her back to reality. After completing a supporting role in Michael Cacoyannis' long in development dream project, an adaptation of Chekhov's "The Cherry Orchard", the captivating, petite Lynskey undertook the supporting role of a friend of a girl whose parents suspect she may be a lesbian in the teen comedy "But I'm a Cheerleader" (both 2000). She rounded out the year co-starring in high profile "Coyote Ugly," and then returned to her Kiwi roots taking the lead in the New Zealand-made road movie "Snakeskin" (2001).
Lynskey made the most of a supporting turn in the romantic comedy "Sweet Home Alabama" (2002) as a childhood friend of Reese Witherspoon's who hangs out in a bar with her baby. Supporting turns in the films "Abandon" (2002) and "Shattered Glass" (2003) and the 2002 miniseries version of Stephen King's "Rose Red" positioned the actress well in Hollywood, but her best exposure came when she took on the role of Rose, Charlie Sheen's soft-spoken, sweet natured next door neighbor and self-proclaimed "stalker" in the hit sit-com "Two and a Half Men" (CBS, 2003- ). After a small part in “Say Uncle” (2006), a satirical comedy about a gay man (Peter Paige) trying to overcome the departure of his only godson, Lynskey joined an excellent ensemble cast for “Flags of Our Fathers” (2006), director Clint Eastwood’s World War II epic that focused on the three surviving U.S. servicemen (Ryan Phillippe, Adam Beach and Jesse Bradford) who raised the American flag during the nightmarish battle of Iwo Jima.