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O'Grady is a native of Detroit, Michigan, the daughter of Jan and Jim O'Grady, a financial planner. She grew up in Wheaton, Illinois, and completed her studies at Wheaton North High School in the year 1981. Prior to shifting into Los Angeles, she appeared in several commercials. The career of O'Grady began as a model and commercial actress with Montgomery Ward. She appeared in 1988's romantic comedy She's Having a Baby and was later a regular role in the ABC comedy China Beach, opposite Dana Delany. She has also guest starred as a guest on independent films and television shows. Donna Abandando was her first big role on ABC's police drama NYPD Blue. O'Grady was the long-haired secretary of the team from 1993 to the year 1996. Her nomination was in the Emmy Award for Outstanding Supporting actor in a drama for every year. In 1995, O'Grady was awarded the Screen Actors Guild Award Outstanding Ensemble Performance in a Drama Series together with the ensemble.