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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 raised her by their parents in Wheaton within Illinois and graduated in 1981, with a degree from the Wheaton North High School. Her appearances in commercials before making the move to Los Angeles in 1986. The first role she had was as a model for Montgomery Ward. She also appeared in several advertisements. She was a part of the 1988 romantic comedy, She's Having a Baby and was then cast as a frequent part in ABC drama China Beach, opposite Dana Delany. Alongside guest-starring on different shows and appearing in independent films and made-for television movies in addition, she was the main character in several television shows. Her first major role was that of Donna Abandando on the ABC Police series NYPD Blue. O'Grady as the large-haired secretariat from 1993 to 1996 received Emmy Award nominees each year for Outstanding Drama Series Supporting Actress. She won the Screen Actors Guild Award in 1995 for outstanding performance by an ensemble of actors in an action series.