From 2002 to 2005, O'Grady starred as Helen Pryor in the NBC television series "American Dreams", which depicted an all-American family living in Philadelphia, Pennsylvania, during the 1960s. The series was canceled after three seasons. In Fall 2005, O'Grady was lead actress in the ABC comedy series "Hot Properties", which was canceled after 13 episodes. In 2006, she guest starred on "Two and a Half Men", and in 2007 had a recurring role on "Boston Legal" as Gloria Weldon, a judge in a personal relationship with attorney Alan Shore. Also in 2007, she starred in the Hallmark Channel movie "All I Want for Christmas".