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The parents of O'Grady include Jim O'Grady who is a financial adviser as well as Jan O'Grady. She grew up in Wheaton, Illinois, and completed her studies at Wheaton North High school in 1981. Her appearances in commercials before moving into Los Angeles in 1986. O'Grady's first job was to model for Montgomery Ward. She also appeared in several advertisements. She made her debut on the screen with the romantic drama Having a Baby in 1988. She later played a regular role in the ABC Drama China Beach alongside Dana Delany. She also guest starred in a variety of other shows and appeared in made for TV and independent films. Her debut role on television was that of Donna Abandando on the ABC Police show NYPD Blue. O'Grady was the long-haired secretary of the team from 1993 until 1996. The actress was nominated for an Emmy Award for Outstanding Supporting actress in a drama for every year. The entire cast as well as O'Grady won an award from the Screen Actors Guild Award of Outstanding Performance in a Drama Series Ensemble in 1995.