Jamie O’Reilly’s childhood sounds like the premise for a Technicolor-drenched 1950s Hollywood musical: a powerful Irish-American, Shakespearean actor father revered in the local theatrical community, a radiant, silver-voiced diva of a mother, and a brood of 14 singing children, each more talented than the next. Put them in a small town in northern Illinois, where they cheerfully perform concerts for needy families and are surprised when the neediest turns out to be their own. As a movie concept, it’s a winner; in real life, it could be a hard-to-follow first act.

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The town was north-suburban Crystal Lake, where O’Reilly’s parents, James and Winifred, raised their family in the theatrical and Catholic-activist traditions O’Reilly’s forebears brought with them when they came to Chicago to work on the Sanitary and Ship Canal. Jamie, their ninth child, was gifted with her mother’s lilting soprano and an impressive range. She studied opera at DePaul University, but by graduation (in 1981) had decided she was more interested in folk music. “After college, the best-paying jobs in folk were in Irish music,” she says. “So that’s what I started out doing.” She married an actor, formed a band–Jamie O’Reilly and the Rogues–had the first of two daughters, and went on the road with Between the Times, a social justice show produced by the liberal Catholic organization Call to Action. After two years of touring she was ready to stay put for a while; by ’92 she had also had enough of the Irish band. “I was never unappreciative of Irish culture,” she says, but she wanted to get out of the pub scene and felt constrained by “the Celtiphile mentality,” which “at that time had an exclusionary factor to it.” She wanted to write her own material, expand her repertoire to other cultures, do things that might be provocative. “I didn’t really have a need to play it safe anymore,” she says.

Performance is still central to her life, but O’Reilly now also sees herself as a writer, producer, teacher, consultant, and coach. She conducts a course, “Self-producing for the Freelance Artist,” at the Guild Complex and Columbia College and is working on a book on the same subject with brother Willem, a writer whose credentials include a doctorate in theater and an MBA.

Art accompanying story in printed newspaper (not available in this archive): photo/Eugene Zakusilo.