Guy (striped shirt) and company outside the Checkerboard, 1982. Photograph: Marc PoKempner. Click image to enlarge.

On the wall by my desk I have mounted a photograph of a confrontation that took place on the sidewalk outside the Checkerboard Lounge, at 43rd and Vincennes on the South Side of Chicago, in 1982. In the picture, the great bluesman Buddy Guy, who owned the Checkerboard back then, faces off against a young man in a hat who has his back to the camera. The young man, ejected from the club after some kind of beef, had stormed off to his car and returned wearing a jacket, with one hand jammed menacingly into one of its pockets. Guy and a crew of his supporters are lined up shoulder to shoulder to bar the way to the door, each privately calculating the odds that the young man really has a gun and would use it. Backing up the boss, from left to right, are Anthony, Guy’s aide-de-camp and security man; L. C. Thurman, who managed the club; and Aretta, who tended bar and waited tables. Standing with them, although he seems more observer or bystander than participant, is Lefty Dizz, a bluesman from Osceola, Arkansas, who hung out at the Checkerboard and hosted its Blue Monday jam for years.

Unlike the others, who strike appropriately forbidding poses—Anthony with drink in hand, Thurman with cigarette balefully pasted in mug, Aretta with hands on hips in iconic disapproval, Guy front and center with his whole being concentrated in the hands-down, shoulder-forward, head-cocked ready position that indicates a willingness to go all the way—Dizz seems bemused, even distracted. He’s the only one not fixing the troublemaker with a grim stare, and he’s holding something soft and bulky in front of him with both hands, probably a balled-up towel, presenting it with palms inward, like an offering or talisman. The others’ body English says, “Mess with me and you’ll regret it.” Dizz’s says, “Life is complex and filled with contingency; this would be a good time to step within for a taste of Old Grand-Dad.”

I like to look at this picture, to which attaches a fugitive whiff of the South Side tavern bouquet of my youth: menthol cigarettes, Old Style beer, and hair treatments made by the Johnson Products Company. And there’s the pleasure of seeing familiar faces, people with whom I exchanged friendly words on nights out in my teens, which means it’s going on 30 years since I used to see them all a couple of times a week. But I also keep the picture around as a reminder to take second and third looks, to revisit scenes and characters and stories that I think I know well.

On that summer night in 1982, Marc PoKempner, a longtime photographer of the Chicago blues scene, happened to pull up to the curb outside the Checkerboard on his motorcycle just in time to shoot a sequence of pictures of the confrontation. I used a different shot from his sequence in a book called Good with Their Hands, published a decade ago. That one was taken from an angle farther around behind the young troublemaker, so that he almost entirely obscures Dizz. Guy has stepped more prominently forward in that one, Aretta’s not in it, and Thurman (who later wrested control of the Checkerboard from Guy) looks off to the side, all of which has the effect of making Guy seem isolated as he attends to yet another problem that an egregio virtuoso should be able to leave to his underlings. I put it in the book to evocatively illustrate Guy’s account of how difficult it was to run a club on the South Side in the 1970s and 1980s.

The version with Lefty Dizz may not be a better picture in the conventional sense—yes, the poses are more dramatic, but the troublemaker’s free hand is blurred, and Dizz, too, is not quite in focus—but it has an added valence that matters. Guy was the marquee name, the guitar hero whose ownership of the Checkerboard gave it a reputation as the capital of Chicago blues and attracted fellow greats like Muddy Waters and Otis Rush, insiders’ favorites like Fenton Robinson and Magic Slim, and rock stars like the Rolling Stones and Stevie Ray Vaughan, who dropped by the Checkerboard after playing sold-out arena gigs. Dizz, the only person I’ve ever met who bore a close resemblance to the Cat in the Hat, was by comparison a minor figure, a local character known for a couple of novelty songs—”I’m sitting here drinking my eggnog, but there’s nobody to drink with me / It’s the 25th of December, and I’m sad as a man can be”—and a gift for orchestrating a good time. He had a droll showbiz manner, and he was a distinctive, if limited, guitar player. He did a great deal of one-handed playing, part of a large repertoire of onstage gimmickry, but he wasn’t all tricks; he had a serviceable blues voice, and he had learned a thing or two about propulsive grooves from the blues-party juggernaut Hound Dog Taylor. Thanks to the quality of local talent and in great part to Dizz, an ideal emcee, the Checkerboard’s Monday night jam was a cut above all others. It usually started out in desultory fashion but built in intensity as musicians, patrons, smoke, inebriation, and sound accrued in the narrow, low-ceilinged room until some magical fission point was attained. On Tuesdays, still lost in the previous night’s music, I’d go around in a daze at school—more of a daze than usual, that is.

Dizz, whose given name was Walter Williams, was the most approachable of the Checkerboard’s notables. A generous fellow and a natural-born enthusiast, he showed a particular affection for the kids from my high school who hung out there. Dizz had studied economics at Southern Illinois University, but he enjoyed playing the down-home blues sage as much as we enjoyed playing at being barflies and connoisseurs. Each indulged the other. I liked to ask technical questions: “How do you make a song yours when other players already made it famous?” He liked to drop aphoristic advice on whippersnappers: “Take your time and listen. Don’t be all in a rush to play fast and blow everybody away. Take your time, and you’ll hear that note in that song that nobody else has heard.” He played an annual gig at my school, staying up all night with his band, the Shock Treatment, to make the early-morning assembly in the gym, where, bleary-eyed in his third-best suit, he performed a short set of his old reliables: “Baby, Please Don’t Go,” “The Things I Used to Do,” “Never Make My Move Too Soon,” “Bad Avenue,” “Somebody Stole My Christmas.”

When I showed up at the Checkerboard with my friends (a 13-year-old with cash in hand had no trouble getting in and buying a drink), he’d purse his lips and give us a mock-serious nod from the stage, and between sets he’d stop by to shoot the breeze. In good weather, we held our between-set colloquies outside the club on the sidewalk, standing around with our drinks in the desolation of 43rd Street, a once-thriving business strip that had fallen upon hard times. A mile to the west, the dark towers of the Robert Taylor Homes marched off along the expressway. They’re gone now, taken down by Daley the Second, but when I was a kid the projects seemed like an immemorial feature of the landscape. I suppose the glaciers seemed permanent as well, when the Laurentide ice sheet covered the upper Midwest.

Dizz is gone too; he died of cancer in 1993. When I look up from whatever I’m writing and gaze for a while at the picture on my wall, he comes back to me.

There’s a lesson I think I’ve learned about creativity: It begins to have import, to take signifying form, to the extent that it is constrained by the conditions in which it’s brought to bear. In my early twenties I tried repeatedly to sit down and write, on my own, in a vacuum, and nothing came out. After a while I figured out that I needed less freedom and more useful constraint: training in the craft, a clearly defined job to do, editors. Magazine editors, in particular, have given me what I need. They have offered assignments, set deadlines, worked over my prose, paid me for my words, and sent me to places and events worth writing about: to Las Vegas and New Orleans, to WrestleMania in Orlando and a fencing academy in suburban Atlanta, to jazz fantasy camp and the Harvard-Yale football game, to polka joints and casinos.

If writing for magazines has given me the structure I seem to need, the equivalent of a gig as emcee of the Monday night jam, it has also given me opportunities to explore longstanding interests. The subjects to which I tend to return offer a pretty fair notion of what I liked when I was 13, or at least of enthusiasms that have lasted: for the blues and other music; for the fights and other sorts of embodied knowledge; for the mechanics and virtues of working at any craft; for city life.

There’s a certain kind of child of the middle class who is attracted to both the street and the library, and who fashions a life out of exploring the relationships between them. Such people form a tribe, and among its members are writers whose work has made the deepest impression on me— Émile Zola, A. J. Liebling, and Jack Vance, to name three. I was 12 or 13 when I began to recognize in myself the twinned attraction to library and street, and to search—vaguely, at first, but with greater purpose as the years went by—for vessels in which to pour that joined interest and give it form as a calling.

It was at that age, too, that I began to realize how libraries and schools were like gyms and blues clubs, all of them institutions where specialized knowledge is ordered and passed along, where one can begin to see how people get good at something. Every library is an incarnation of the Library of All Time and Space. Every school, from kindergarten to research university, is a branch office of a single world-spanning enterprise: Big School. Every bar, whether it offers live music or not, is a touchingly imperfect copy of the One True Bar. The Mystical Body of Boxing Gyms is manifest in a strip-mall storefront with a duct-taped heavy bag hanging in the corner or in a converted industrial loft just big enough for a sparring ring. In my early teens I began to see such permutative places as my habitat, structural elements of the world I wanted to live in, and to realize that the lessons on offer in them were the lessons I wanted to learn.

As an essayist and reporter I tend to be most comfortable at ringside, on the close margin, inside the scene but ceding center stage to headliners like Guy and the troublemaker in the hat. And yet I recognize that inevitably there’s a kind of self-portrait between the lines in the kind of work I do. The figure somewhere between observer and participant whose presence is implicit even when obscured, the figure emerging into view in the second-look Lefty Dizz version of experience that nonfiction writing pursues, is me.

Carlo Rotella is a professor of English and American Studies at Boston College. He writes regularly for the New York Times Magazine, the Boston Globe, and the Washington Post Magazine. His essay is drawn from the introduction to his most recent book, Playing in Time: Essays, Profiles, and Other True Stories (© 2012 by Carlo Rotella), with permission of the University of Chicago Press.