The urban legend about painting the Golden Gate Bridge—by the time the crews finish, they have to start over again—could just as easily be about the task of profiling every interesting person in the Chicago music scene. Thankfully that's not what we at the Reader have set out to do with our second annual People Issue. Nor do we mean to tag along after the celebrities of the moment—though if you follow music in Chicago, you've likely heard of at least one of our B Side subjects. In fact you might say the idea is to give you a glimpse of the profusion and diversity of talented, committed people who pursue their passions outside the glare of the spotlight. These are people who could be friends of friends, or sitting across from you on the train. From the stories that follow, told entirely in their own words, you'll learn as much about them as if you'd shared an armrest for a transcontinental flight—maybe more, if you're not the sort of person to start conversations on planes.

Singer-songwriter Angel Olsen, who was making mixtapes of herself singing along to Mariah Carey and Whitney Houston at age 12, went from playing house shows on the roof of Miko's Italian Ice in her teens to touring with Will Oldham. DJ Dave Matta turned his obsessive crate digging into a way to give his music students at a charter middle school a window into different cultures. Jazz vocalist Dee Alexander has patiently nurtured a music career while raising a family and holding down a day job at the Office of Research Services at the University of Illinois, and next year she'll appear for the first time at the legendary Newport Jazz Festival.

Gay music writer and photographer Vern Hester called upon his Buddhist faith to help him recover his health when he almost died in 2003 after living with HIV for 20 years; "I wanna be a dirty old man," he says, "and I wanna shoot rock 'n' roll." Club-culture maven Zain Curtis, aka Teen Witch, first held his monthly CULT dance party three years ago for an audience of five, but CULT has since helped cultivate an underground aesthetic that caught Rihanna's eye. DJ and producer Million Dollar Mano started out spinning at abandoned houses in high school, but last year he became one of the DJs on Kanye West and Jay-Z's Watch the Throne tour.

That's just the tip of the iceberg, of course—or, if you like, the first few yards of the bridge. Except that sharing these stories with you hardly feels like work.