ELF ESTEEM Santa takes the mike in Judy Kropsch’s “Windy City.

Architect Daniel Burnham’s exhortation to “make no small plans” would be an apt motto for the Chicago 360 documentary project, which aims for the cumulative creation of a ten-hour mosaic portrait of the city, its culture and its people over the course of a decade.

The project, sponsored by nonprofit film-production company Split Pillow, began in 2006, when five local filmmakers were each given $360 to make a ten-minute minidoc about some facet of Chicago life. Linked with transitional materials, the five segments became a 60-minute omnibus titled Chicago 360, which has proven itself a crowd-pleaser in screenings at Chicago Filmmakers, the Music Box Theatre and a variety of local art spaces. The master plan for the enterprise calls for this creative cycle to be repeated every year through 2016. 

The 2007 installment premiered at Chicago Filmmakers on April 20 and will play there for the next three Fridays. Titled Chicago 360 v.2, the film kicks off with Judy Kropsch’s “Windy Season,” a brisk and (given its modest budget) surprisingly professional-looking history of the observance of Christmas in the great retail palaces of State Street, where the iconic department-store Santa was reportedly born. Kropsch, 45, says her favorite childhood memories are “all about Santa Claus  and downtown,” but nevertheless felt obliged to incorporate an accurate proportion of footage of children traumatized to tears by their personal encounters with St. Nick. “I had to represent that because it’s true,” she says with a laugh. “The idea of Santa and the reality are two different things for kids.”

The following segment, Melina Kolb’s “The Original Slam,” documents what’s said to be the world’s longest-running competitive poetry showcase. Founded by Chicago poet Marc Smith, the series has been a weekly event at the Green Mill since 1987, and judging from Kolb’s film, is a raucous good time. “I found out about the Green Mill poetry slam about a year ago from a friend who’s a slam poet,” says Kolb, a 22-year-old U. of C. anthropology grad. “Right away I thought, Wow, I should do a film about this. So when the Split Pillow project came along I had my subject ready.”

Next up is Jackie Sestak’s “Chicago on Chicago,” an affectionate group portrait of three small businesses—an indie coffee shop, a quirky toy store and a self-consciously retro diner that advertises “good food and bitchy waitresses”—clustered in the hipster hinterlands on the southern boundary of Ukrainian Village. It’s followed by Etta Worthington’s “Chicago Swingers,” a cheerful survey of the sweetly nerdy subculture of Chicago swing dancers. 

The anthology ends on a disconcerting but affecting note with “No Half-Steppin,’” Tom Bailey and Brenden Kredell’s portrait of Brian Wharton, a.k.a. Sharkula, an intermittently homeless and psychologically troubled 33-year-old rapper who subsists by peddling his self-produced CDs on the street while dreaming of impending superstardom. As Kredell acknowledges, it’s the sort of doc that’s vulnerable to charges of exploitation. “We were very conscious of our status as filmmakers who  go home to warm beds,” he says. “With a project like this, you want to maintain respect for your subject without papering over the realities of his situation. But whenever we defined Brian by his problems, we’d hear about people in, say, Kentucky, who really love his music, or meet people  who buy all his CDs. The ethical pitfalls are the same ones you’d encounter with any outsider artist,  and I hope our efforts to get the tone right have paid off.”

Recently all the filmmakers sat down to see a rough cut of their combined labors. “It was  interesting to see the diversity of subject matter, but even more fascinating to observe all these tangential connections among the films,” Kredell says. “The Santa Claus film and ours struck me right off as being similarly out of left field in terms of depicting odd personalities. What motivates a guy to dress up as Santa Claus is the same sort of need to be at the center of things that motivates Sharkula. Even the lady who runs the diner  is putting on a show. It’s  cool to think about these subcultures coexisting in the same moment, and  also  about how the films are  going to look in relation to whatever  new  layers are added to the project over time.”

For information on getting involved in the project, visit www.splitpillow.com