Musicians Aimee Mann, Joe Henry, and Loudon Wainwright III gather in Louisville to indulge in raw oysters, dry martinis, and unscripted conversation.

We were en route to the shoot’s first location in Butchertown. My brother David was leading us to Please and Thank You on East Market Street. David has lived in Louisville, Kentucky, for some 20 years, and he had brought us—me and fellow singer-songwriters Aimee Mann, John Doe, Karin Bergquist, and Loudon Wainwright III—to the city to appear in a feature film he had cowritten.

It was our first morning in town, and Please and Thank You (P&TY) was the perfect headquarters for those of us looking to shoehorn our way into the snug demands of the day, whatever they might be, and it provided our first insight into Louisville’s artisan bent and hipster funk.

Berlin Art

P&TY not only makes excellent doppios and home-style baked offerings—including scratch doughnuts that rival those made at the Michigan cider mills of my youth—but also features along one wall a seriously curated collection of vinyl records for sale. If a café pulls an exceptional, nutty-tasting shot of espresso, offers me baked strata of egg and roasted vegetables fresh from the farm stand, and serves them both while spinning Bringing It All Back Home in original Stereo 360 Sound, that place will own me for the duration of my stay.

At the close of day one of filming, the five of us, along with my brother (still kindly acting as our escort), gathered for our initial dinner together at Jack Fry’s on Bardstown Road in a neighborhood known as the Highlands.

“This is terrifying,” I heard someone say, and then realized it was my own voice. We were musicians working as actors playing musicians, several of us having stepped well out of our comfort zones to do so.

All of us involved in this venture—a film called Pleased to Meet Me, directed by Archie Borders and based on a story originally produced for the radio series This American Life—are touring musicians. Far from home, we form quick impressions of cities based on a very few elements of comfort and engagement. We’d arrived in Kentucky’s largest city from Los Angeles (two of us), the San Francisco Bay Area, Ohio, and New York, and we’d come for two and a half weeks. An almost unheard-of stay in a single location for most of us, the time in Louisville gave us a chance to establish roots of a sort, and to read the city’s tea leaves in something more like three dimensions.

Louisville Joe Henry

Modern Louisville is, as we would discover, much more than the home of the Kentucky Derby. Once a crucial hub of river and rail transport, the city is an anomaly in its region, a patch of blue in a sea of red, politically speaking. It fosters gallery hops, live theater, a thriving dance community, an influential music scene, and a culinary movement at once folksy and progressive, with something for organic farmers and steak-and-martini hounds (can I get a witness?) alike. Responding to this last note, the five of us principals formed the Diners Club. We hunkered down together as if in the army, trading offerings of fine food between us like canned rations and cigarettes in a wartime foxhole. The restaurants we invaded became the frames around whatever picture the day had formed, reminding us how often the most revelatory conversations take place between people with forks in hand.

Established in 1933, Jack Fry’s is a classic steak and chops house. At an old-school spinet piano, a polite man proffers jazz standards at a volume that accompanies rather than inhibits conversation. The menu, likewise, sings from the great American songbook, though with a modern flair: Rare lamb chops, for instance, arrived with potato gratin and shiitake mushrooms. It was a theme we continually noted in Louisville. Like high-flying kites that must be tethered, the boldest culinary choices were invariably rooted in tradition.

We hit Jack Fry’s three times during our stay, the third visit by request of the evening’s birthday celebrant, Aimee Mann, who devoured her herb-encrusted seared pork chop with a fervor that belied her Lauren Bacall–slim frame. But then, she is full of surprises. For all her well-earned reputation as a cloistered chronicler of hurt and dysfunction, Aimee is a riot when out of the house. At one point, the conversation turned to the actor/activist Sean Penn, who is Aimee’s brother-in-law (and, coincidentally, used to be mine many years ago, when Sean was married to my wife’s eldest sister, Madonna). Sean’s unpredictable, live-wire actions in the greater world provoke high anxiety in those who count themselves among his legal relations. “Let’s just say that where my in-laws are concerned,” Aimee offered flatly, “it’s frequently best not to answer the phone. Or the door. Or to have a door.”

We wrapped fairly late on the set one evening toward the end of our first week of the film shoot. We’d all learned to relax a little, since our director seemed pleased with the way things were going: The scenes felt spontaneous—raw and fresh, and rarely overwrought. Not sure where we might still find a good, unhurried sit-down dinner together, the Diners Club was steered back down East Market Street by a local, the cinematographer Mike Fitzer, to an excellent restaurant called Harvest.

The specials included an appetizer of fried okra, special indeed to someone like me, who originally hails from North Carolina. As I do when cooking it at home, the chef sliced thin wheels of hot pepper in amongst the okra so that the occasional forkful brought with it a single bright spark of heat. Thus primed, I elected to go all-in Southern style, ordering the fried chicken with biscuits and white gravy. At the far end of the table, Karin Bergquist rhapsodized over her order of tender gnocchi with vegetable ragoût. Karin is from southern Ohio, where she lives on a pre-Civil-War-era farm with Linford Detweiler, her husband and partner in the band Over the Rhine. She trains a skeptical eye on the world at all times, which made her delight all the more satisfying. “We might both come from white trash, Joe Henry,” Karin offered without raising her head from her entrée, “but we’re no pushovers.”

Speaking from the business end of his special Harvest pizza, Loudon Wainwright III shared stories of his small role in the 1989 film Jacknife, which starred Robert De Niro and Kathy Baker, in particular his apprehension at having to go mano a mano with De Niro in one scene. For the uninitiated, Loudon is one of the most original American singer-songwriters of both the last century and the one in progress. His body of work—simultaneously deeply personal and universal—has helped to sharpen the blades and focus the lenses of most all of us who have followed in his wake.

“He wasn’t terribly articulate out of character,” Loudon said of De Niro, “but he managed to advise me that I needn’t worry about the script word for word. Rather, I just needed to let the character move through the arc of the scene, in any way that felt natural.”

It’s something we all would witness Loudon do time and again throughout the course of filming. Even in a scene in which he had two words, or none, Loudon’s performances were a crash course in film acting for the neophyte, reminding me how much singing is, in fact, an actor’s game.

Berlin Art

In the spring of 1983, I was 22 and living in Ann Arbor, Michigan, where I was recording my first demos. I drifted over to the Michigan Theater one evening to see Minneapolis’s reckless wunderkinds the Replacements. They disappointed me greatly, refusing to play most of the songs through to the end. I was on the verge of walking out when a friend urged me to stay for the headline act, X, the blistering, rootsy punk band from Los Angeles. I stayed, and what I beheld made me reconsider altogether the cathartic vitality and singular relevance of rock-and-roll music, which I had felt was on the wane.

Cut to Louisville. John Doe, the cofounder and chief songwriter of that seminal band, sat to my left in Proof on Main, a restaurant within the elegant and hip 21c Museum Hotel. Sharing the hotel’s ethos of merging the timeless with the contemporary, the good people at Proof set before us old-world sustenance that leaned decidedly forward: hearth-warmed ricotta, homemade pastas, and a bison burger with bacon and Tillamook cheddar.

John Doe is a legendary character upon our landscape: rakishly handsome, tough as nails, and sweet as pie. He is also fiercely candid and, when asked, shares his wild experience with the generosity of a scoutmaster. Raising a Manhattan in my direction, John spoke freely about the fresh row that bands like X had hoed alongside their confederates, Los Lobos and the Blasters, when they started. “We loved country music,” John offered, by way of disguishing X from the early punk bands of Britain, “and real country music— George Jones and Merle Haggard, sure, but also Woody Guthrie, Lead Belly, and Lightnin’ Hopkins. We also were products of electricity—the Who, the Faces, the Flamin’ Groovies. We played faster and louder because the times were.”

As we neared the end of our shooting schedule, and thus our time in Louisville, the Diners Club managed to secure a table at chef Edward Lee’s storied 610 Magnolia—a handsome, cozy room on a quiet residential street in the oldest part of the city. The restaurant was closed on the night in question, but a few strings were pulled and we were welcomed and accommodated, even at an uncommonly late hour for people who let dinner and its attendant conversation unspool slowly for hours. I stepped out of the rainy darkness straight into a dry martini, heard Ray Charles drifting down from the rafters, and knew I was at home, so to speak.

Berlin Art

Lee’s approach to Southern cuisine is observant of traditions but in no way trapped by them, a slant that was coming to define our experience of contemporary Louisville. I was happy at the suggestion that, rather than peruse a menu, we sit back and let the soft-spoken young chef de cuisine, Nick Sullivan, devise our fortunes. And fortunate we were, with dishes from smoked octopus and lobster medallions to pork belly, seared lamb, collard greens, and an heirloom grit cake.

Aimee and John wouldn’t materialize until joining us for a nightcap at last call, as they were on the graveyard shift shooting our film’s final scene, but the occasion insisted we push on without them: It was Loudon’s birthday. As a gift for Loudon, I had purchased two rare County Records albums by Charlie Poole (along with other original vinyl pressings) at Please and Thank You. In 2009, Loudon won his first Grammy Award for a project inspired by that raucous country music pioneer. It was fitting, then, that so much of the evening’s conversation concerned our collective debt to so many early folk luminaries.

“The mythology that gets passed along is very seductive,” Loudon submitted, “especially because it suggests that the music has all trickled down from a very few geniuses. But in fact there were many significant journeymen out ahead of us, shining their light along the path, equally as visionary—and troubled—as, say, Jimmie Rodgers or Hank Williams. Charlie Poole was just one of them.”

The one table we returned to most frequently—the place that came to feel both special and familiar—was La Coop, a French-style bistro, also on East Market Street. We came to it, initially, following an early day of filming that I might characterize as “trying.” We had spent a dozen hours in a warehouse studio that was 90-plus degrees with humidity to match. Karin, Aimee, John, and I straggled into La Coop fearing we had missed the kitchen’s last call, only to find ourselves warmly greeted and ushered to a back table, with the full menu on offer. Reality was setting in for those of us new to the rhythms of a film shoot. Though we were excited by the prospects, we (read me) were daunted by them as well, but it was nothing that a little chilled gin and several raw oysters couldn’t undo.

Louisville Joe Henry

The decor at La Coop is mod but with enough dark, nostalgic ambience to assure you it is helmed by someone with Edith Piaf records in the collection. We passed around steamed mussels and duck fat fries before even a cursory glance at the menu, and did so with giddy relish. I am a polite traditionalist where a bistro is concerned, which means I hum and nod admiringly as the specials are read, and then I order a rare steak frites and an arugula salad, the communion attended by the ritual house Bordeaux.

We talked a lot about how much recording and filmmaking have in common, a musical performance being akin to live theater, and making an album being like conjuring a movie. “Singing is first an acting gig,” said John, mirroring Loudon’s earlier example. “You’re always putting some character forward and asking people to believe in him.”

“And the third verse is invariably like the third act, I suppose,” added Karin, “all of us looking for redemption. Or at least a back way out.”

When we finally wrapped the film shoot, the director, Archie Borders, and his new wife, Anne, along with my brother David and his wife, Clare Hirn (a painter of no small renown in Louisville), joined the club for one last celebratory bread-breaking at La Coop. We visitors were all every bit as enamored with Louisville as we had been, naively, upon our arrival. The initial impression, then, was borne out: Louisville as a community has made choices favoring vision, craft, and character—respectful of tradition while actively breaking new ground.

Thanks to our intense shooting schedule, I had seen very little of the city beyond my hotel room, two set locations, and the aforementioned eateries, yet I departed feeling we had all gained a surprisingly comprehensive sense of what makes Louisville unique.

“How you do anything is how you do everything,” singer Tom Waits once said. Based on our Diners Club experience, I’d be inclined to return to this old city along the Ohio River to have my boots repaired or my appendix removed. In either case, my belief is that the work would be done with quiet passion and unstinting commitment, and with a decent coffee offered while I wait. A

Photos by Michael Wilson. This appeared in the May 2013 issue.