O'Grady played the big-haired squad secretary from 1993 to 1996, and for each year received an Emmy Award nomination for Outstanding Supporting Actress in a Drama Series.

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.

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.

[7] O'Grady had regular roles on the short-lived CW series Hidden Palms as Karen Hardy in 2007, and on Hellcats, playing Wanda Perkins, the mother of the main character, from 2010 to 2011.

In 2008, she had a recurring role on the ABC series Desperate Housewives as Anne Schilling, a woman who is having an affair with the character Porter Scavo (at that point a teenager).

[8] She appeared on Monk, CSI: Crime Scene Investigation, The Mentalist, Law & Order: Special Victims Unit, Drop Dead Diva, Hawaii Five-0, and Castle.