In 1998 Clarkson put in a bitterly funny performance in High Art, playing Ally Sheedy's heroin-addict girlfriend. This marked the start of higher-profile roles for Clarkson. She appeared in 1999's The Green Mile, The Safety of Objects (2001) and actor-turned-writer/director Sean Penn's The Pledge (2001). She also appeared in Far From Heaven (2002) and director Lars von Trier's experimental Dogville (2003). In 2003, she won several film honors for her role of a grieving mother in the lauded independent film The Station Agent and received a Best Supporting Actress Oscar® nomination for her work in Pieces of April. In 2004 Clarkson appears in The Miracle, about the 1980 U.S. Olympic hockey team that beat the U.S.S.R. in one of sport's greatest upsets.