Bob Rohrman’s effusive car dealership commercials have aired—frequently—in the Chicago area for many years. “I grew up here,” says Josh Schollmeyer, the writer of Why Is This Man Smiling?

“He’s been the white noise of my life.” Schollmeyer’s interest was piqued by the apparent contrast between Rohrman’s jovial onscreen persona and his recent lawsuit accusing a plastic surgeon of stealing his wife away. “That [television] image, that’s him,” Schollmeyer says. “He’s Laughing Bob. He’s always having fun.” But Schollmeyer observed another side of Rohrman, too: “Make no mistake—he’s nobody to mess with.” Schollmeyer shadowed Rohrman for several days from 8 a.m. till almost midnight, learning about the tycoon’s car-sales empire, his personality quirks, his sense of humor, and that lawsuit. Despite the notoriety of the case, Schollmeyer says Rohrman remained remarkably open about his life and thoughts. “His lawyer’s like, ‘You need to learn off the record,’ ” Schollmeyer says.

“He’s got this laugh I can’t describe,” says TAYLOR CASTLE, who photographed Bob Rohrman for Why Is This Man Smiling? “Kind of like the Cowardly Lion—mouth wide open, gasping for air.” Laughing almost constantly, Rohrman hammed it up for the camera and also showed Castle’s crew a few things behind the scenes at a dealership, including what Rohrman called his Mardi Gras ties (“Amazingly hideous,” Castle says) and his hot tub with gold-plated lions. “He tried to sell me a Lexus at the end of the shoot,” Castle says. Castle’s work has appeared in Fast Company, Men’s Journal, and ESPN The Magazine.

For “In Their Sights” in Reporter this month, JENNIFER TANAKA headed into the research thicket of an area unfamiliar to her: the litigation over handgun possession laws. “I was a rank amateur trying desperately to come to grips with constitutional law,” says Tanaka, a senior editor at Chicago. After wrestling with the doctrine of incorporation and the due process clause, she wrote up the story to illustrate the personalities and elucidate the issues to someone like, well, herself. “I wanted to impart rich context to what otherwise might be a profile of four people,” she says, “because really, they’re four people involved in a news story, not just four people.”

The Soul of a New Building follows the tortuous maneuvering behind planning a work of architecture—here, the Salvation Army’s community center in West Pullman, due to break ground this spring. “What I really like to do is use narrative as a means to talk about architecture,” says JAY PRIDMORE, who writes frequently on architecture for Chicago. Every building has a story that tells how it is shaped by outside forces—economics, politics, philanthropy, and even, in this case, theology. Those pressures can ultimately enhance, rather than inhibit, the vision of the architect. “Frank Lloyd Wright suggested the best architecture was produced under circumstances where you had to do the most with the least,” Pridmore says.

No two photo shoots are alike. When KATRINA WITTKAMP photographed this year’s Chicagoans of the Year (Action Figures), a shoot at a therapeutic horseback riding center ran into a problem she’d never encountered before: gnats. “They were landing on my lens, in my mouth, making the horse rear up,” she says. Relocating to avoid the bugs, she stumbled onto a picturesque setting in a nearby forest preserve, serendipitously finding the perfect backdrop. When photographing another honoree, Wittkamp set up shop at dawn across the tracks from a parking lot near Soldier Field—on a Bears game day. As the sun came up, so did the barbecues and loud rock music. “I got home at 9 a.m. and made a brat for breakfast,” she says.

Photography: (Schollmeyer) Katie Basil, (Castle) Stephanie Bassos, (Wittkamp) Katrina Wittkamp