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O'Grady is the daughter of Jim O'Grady and Jan O'Grady. Jim O'Grady works as an advisor to financial institutions. Her family was from Wheaton, Illinois, and was a graduate of Wheaton North High School in 1981. She appeared as a model in commercials for a time before relocating into Los Angeles. O'Grady began her career modelling at Montgomery Ward and making commercials. She played a role in the romantic comedy She's Having a Baby and was later cast as a recurring part in ABC comedy China Beach, opposite Dana Delany. Additionally, she appeared in a variety of shows. She appeared in both independent and made for TV films. Donna Abandando was her first major role on ABC's police thriller NYPD Blue. O'Grady was the big-haired team secretary of ABC's NYPD Blue from 1993 through the year 1996. Each year, she received Emmy Award nods for Outstanding Actress for the Drama Series. Along with actors, she received the Screen Actors Guild Award for Best Performance by an Ensemble in a Drama Series in 1995.