Kelly starred in the CBS drama "To Have & to Hold" opposite Jason Beghe before playing Mandy Hampton in the first season of "The West Wing". In 2003, Kelly began playing single mother Karen Roe on the teen drama "One Tree Hill". She also directed two episodes of the series: "Resolve" (2007) and "I Slept with Someone in Fall Out Boy and All I Got Was This Stupid Song Written About Me" (2006). In the fifth season, she ceased to be a regular cast member, but made guest appearances in the 100th episode and the sixth-season finale. She has made guest appearances in television shows such as "Heroes", "Law & Order", and "Numb3rs". Kelly has also appeared in the films "Remember the Daze", "A Smile as Big as the Moon", "Taken Back: Finding Haley", and "Girl in the Bunker".