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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. She was raised in Wheaton, Illinois, and was a graduate of Wheaton North High School in the year 1981. Prior to shifting from Illinois to Los Angeles, she appeared in commercials for a number of companies. O'Grady's early career was as an Montgomery Ward model, where she was also featured in several commercials. She began her career on the screen with the romantic drama Having a Baby in 1988. She later played a prominent role as a recurring character in ABC comedy China Beach alongside Dana Delany. In addition, she guest-starred in a variety of other shows as well as appeared in made-for TV and independent films. Donna Abandando is her first part as a main role in ABC's NYPD Blue. O'Grady, who played the long-haired, secretariat character from 1993 until 1996 was among the Emmy Award nominees each year for Outstanding Drama Series Supporting actor. She won the Screen Actors Guild Award in 1995 for outstanding performance by the cast of a drama series.
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