• Winifred O’Reilly, still smiling after 14 kids

Thirteen years ago, the New Yorker published what turned out to be a famous article by Malcolm Gladwell called “Six Degrees of Lois Weisberg.” It wasn’t really about Weisberg—Chicago’s former cultural commissioner, currently selling exotic fruit in Florida—but it dwelt on her as a great example of a connector: somebody with a special gift for bringing together loads of people.

Winifred O’Reilly is a connector, too—only she went about it the old-fashioned way, by having and raising 14 children. You read that right.

A onetime singer, Winifred (nee Giebel) married actor James O’Reilly and founded a dynasty that includes some of the most interesting and valued members of Chicago’s fringe community. Her fifth kid, Beau, is especially famous as a founder of the sui generis band Maestro Subgum and the Whole, its theatrical off-shoot the Curious Theatre Branch, and the annual fringe extravaganza known as Rhinofest. Beau’s sons Colm O’Reilly and Rory Jobst are making their bohemian presences felt here, too—the former as a member of Theater Oobleck, the latter as a playwright. Add in the performing families with which the O’Reillies are allied by marriage and/or affinity—the Amandeses (Tom and Paul) and the Magnuses (Jenny and Bryn), for example—and you start getting a sense of just how far this commonwealth of creativity extends.