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The parents of O'Grady have been Jim O'Grady who is a financial advisor as well as Jan O'Grady. She was raised in Wheaton and went to Wheaton North School, graduating in 1981. She appeared in a few commercials prior to moving into Los Angeles in 1986. O'Grady began her career modeling at Montgomery Ward and making commercials. She was the star of her debut on the big screen in the 1988 romantic comedy She's Having a Baby, and she was later cast in the recurring role of ABC Drama China Beach opposite Dana Delany. The actress has also appeared as a guest and appeared on independent movies as well as television series. Donna Abandando, her first significant role in the ABC detective comedy NYPD Blue was the character she played. O'Grady was the long-haired secretary of the unit from 1993 to the year 1996. She was nominated in the Emmy Award for Outstanding Supporting actress in a drama each year. In 1995, O'Grady was awarded the Screen Actors Guild Award Outstanding Ensemble Performance in a Drama Series alongside the entire cast.