Downtown Knoxville juxtaposes prosperity and destitution. Purpose and aimlessness. Ease and suffering. Hope and hopelessness.

At dawn, joggers in the main commercial corridor share sidewalks with the unhoused, neon HOKA runners clipping along past drab sleeping bags.

A few blocks away, bus riders wait standing at a transit stop where benches double as beds for half a dozen homeless.

Across the street, lawyers and municipal bureaucrats arriving for work rub shoulders with last night’s drunk tank detainees in the cloister of a neo-Georgian courthouse.

Later, back in the the central business district, small children romp on a splash pad next to an elderly woman washing her feet. In an adjacent green area, a couple sits on a towel just a few feet from a man in a trapper hat playing the drums on a discarded baking pan.

That evening, restaurant-goers pretend not to hear the profanity-laced portents of a street seer prophesying from a nearby pavilion.

After dinner, girls in red gingham dresses serve ice cream to a crowd lined up out the door of a popular dessert shop. On the same corner, a woman in a wheelchair, possibly paraplegic, plays a melodica.

Prosperity and destitution. Purpose and aimlessness. Ease and suffering. Hope and hopelessness.

Knoxville isn’t unique in counterposing joy and pain, of course. The same juxtaposition’s on full display in downtowns across America, where the soaring cost of housing post-pandemic exacerbated what, in some locales, was an already severe homelessness crisis.

But the adjacencies are particularly striking in cozy Knoxville where, in addition to being tragic, Dickensian socioeconomic juxtapositions are ironic. Downtown’s homey vibe makes the presence of so many unhoused as odd as it is heartbreaking.

The nearness of the suffering’s psychologically uncomfortable from a “There but for the grace of God go I” perspective. But it’s the contrast between the already stark circumstantial disparities and the deliberately down-home atmosphere that makes the whole scene feel surreally — cruelly — incongruous.

I visit, sometimes for long stretches, so I can remember what it was like to be alive. Knoxville’s where I found myself. Or, more accurately, where I created the version of myself that every subsequent version’s nostalgic for.

I tell anyone who’ll listen that “Knoxville me” was the authentic version. Maybe that’s true, maybe it isn’t. Or maybe it’s nonsensical through a Heraclitean lens.

To the extent it’s true, it’s not something I should be especially proud of. Pursuing authenticity in oneself as a mode of being while fully cognizant that one’s core convictions are morally deficient is selfish at best. At worst, it’s societally injurious.

Downtown’s contiguities put me in touch with one of the more desperate denouements associated with the suffering my authentic self contributed to in the city so many moons ago.

The absence of any literal, straight-line cause and effect relation’s exculpatory in a temporal sense. The chronological dislocation alone means the odds of a linear connection between the sins of my former self and the plight of the baking pan drummer or the pavilion preacher are infinitesimal.

But I doubt that’ll be exonerative in the court of divine judgement, where some self-righteous celestial prosecutor will surely say such distinctions are without a difference. Eadem, sed aliter.

Misplaced nostalgia isn’t the only reason I (re)visit Knoxville. I delight in morning jogs and downtown’s a runner’s paradise. From the front door of Hotel Cleo I cross an empty predawn Gay Street, head “straight” through Charles Krutch Park, down Clinch Avenue, over the Henley Street Pedestrian Bridge, down the steps by the Sunsphere and into the World’s Fair Park district.

From there, I climb one of several hills to campus and wind through the university where my Dr. Jekyll side was a domineering Master’s candidate famous for fashionable lateness, long-winded harangues and abrupt exits that left the faint bouquet of Old No. 7, Acqua di Giò and cutting agents as the only testament to his having been there at all.

On the return, I jog down past the Wayne G. Basler Boathouse, through Volunteer Landing Park and up the impossible Walnut Street incline, returning to the hotel just as morning rush hour — or what counts for rush hour in a town that small — gets going.

I don’t know how far I run. Far enough to be famished. There’s a cafe across the street from the Cleo in the lobby of another hotel. Their cappuccinos aren’t much to speak about, but they have a wondrous selection of supposedly handmade bagels. Whether they’re actually made by hand I have no idea. I doubt it. It doesn’t matter. The French toast variant’s heaven. I order two.

After that, I don’t eat until dinner, which is to say I save the rest of my runner’s appetite for evening restaurant tours that typically span four or five hours and three or four restaurants. It’s a teetotaler’s version of bar-hopping, and it’s one of my greatest joys in sobriety.

At the risk of stating the obvious, Knoxville’s no New York City if you’re a real gourmet. Downtown boasts dozens of restaurants, only one of which would suffice for a genuine gastronome. But I’m just an ersatz epicurean; a faux bon vivant. My pretensions to high-society would have it otherwise, but my palate’s not especially refined.

Downtown has three main restaurant “districts,” if you will. Gay Street, Market Square and old city, near the railroad tracks. Old city’s in the third decade of a gentrification push aimed in part at accommodating a new baseball stadium. The facility, which celebrated its grand opening last year, is uncomfortably proximate to an open-air heroin market operating out of a homeless encampment under the interstate.

That latter bit sounds sad — sorry, is sad — but it’s also historically consistent. A website dedicated to the old city recounts an “extraordinarily complex” history for an area that “occupies only a few linear blocks.” Those blocks, the site notes, “once contained the region’s highest density of saloons and, for a while, Knoxville’s red-light district.”

Time was, you didn’t go to old city for dinner and you surely didn’t want to live there. You went to shoot pool and drink pitcher beer at dive bars that served fried mushrooms and onion rings. As the The Old City Association puts it, “the neighborhood was long known for its ups and downs, and at the turn of the century was coming to seem almost purely a nighttime attraction, many of its restaurants and bars not even open in the daytime.”

That began to change around the time I arrived as an undergraduate at the University of Tennessee. But it’d be another decade before efforts to convert buildings like the old JFG Coffee factory into upscale lofts gathered real momentum. Today, old city’s recognizably gentrified, even as the transformation remains conspicuously incomplete. Suffice to say you can get a $900,000 loft, a $12 latte and a $45 haircut in old city. You can also step on a used needle if you’re not careful.

I preferred the “authenticity” of pre-gentrification old city. Jim Beam shots, pool and button mushrooms pulled from a dirty fryer. Gentrified old city doesn’t much appeal to me, so I stick mostly to Gay Street and Market Square for my restaurant-hopping.

On Gay Street, there’s Lilou, the elaborately-decorated brasserie underneath the Cleo, where a disinterested bar staff will absentmindedly serve you passable versions of French clichés like escargots à la bourguignonne and duck confit. Occasionally, they’ll commit an egregious error like forgetting to warm up the sauce au chocolat for your profiteroles. But unforgivable as such faux pas would be in Paris, they’re easy to laugh off in Knoxville.

There’s Nama, which boasts “the best sushi menu” in town, as management puts it. That’s a bit like Lilou saying they have the city’s best caviar martini: The claim’s probably true, but it leaves out important nuance, namely that when it comes to sushi, let alone caviar martinis, there really aren’t a lot of options in Knoxville.

There’s also The Kennedy, a relative newcomer which doesn’t realize that as trendy dining concepts go, “sophisticated yet relaxed” is the furthest thing from “unique.” The menu reflects a similar heedlessness. A wagyu burger with onion rings is the response you’d get if you told ChatGPT to stereotype “pretentious but humble” in a culinary context, and as such suggests an almost pathological insensibility to cliché.

Besides, if it’s a “gastropub” experience you’re after, Knoxville already has that in Market Square, at the Oliver Royale, where a burger on whole grain with welsh cheddar, Benton’s Ham crisps, apple chutney and a local farm egg is what The Kennedy’s wagyu burger hoped to be. Also in Market Square: A sports bar, a dive bar, a Tex-Mex spot, an overpriced, vegan-friendly gourmet pizza parlor called Tomato Head and Emilia, which bills itself as “handmade Italian.”

Away on their own are Pete’s and Chesapeake’s. If you’re the type who insists on a “real” breakfast — where “real” means the sort of breakfast modern cardiology would advise you to avoid at all costs — Pete’s has you covered. A veritable downtown institution, Pete’s has been serving eggs, bacon, sausage, home fries, BLTs, biscuits and gravy out of the same window-fronted diner for more than 40 years.

Just down the hill is Chesapeake’s, another throwback. Opened in 1982 when more than 10 million people visited the city for The World’s Fair, the original downtown location’s a time capsule. It’s dark in there, there’s a lot of wood and a waitstaff dressed in black ties and aprons over crispy white button-downs won’t get the joke if you tell them you’ve been given 1985’s menu by accident. (“Ok, well then I’ll have shrimp cocktail and Maine lobster with drawn butter.” “Anything else?” “Nope, that’ll do it.” “You sure?” “Ummm, yes but… crab bisque?” “Good, very good.”)

On the first evening of a three-day stay in early-July, I stepped out for dinner wearing something that nodded politely to the compulsory local color palette. In Knoxville, you’re supposed to wear “Tennessee orange.” That’s a pretty big ask: It’s a rare soul who can pull off orange anything, to say nothing of an entire ensemble centered around one distinctively obnoxious shade of it. But, to avoid running afoul of local code, I wore a natural cotton twill worker jacket from Gallery Dept. with the “French logo” — the “DÉPT. de la GALERIE” stamp — printed in orange on the back.

Gallery Dept.’s an example of humble pretentiousness, but wearing luxury LA streetwear in 2026 is a bit like putting a wagyu burger on your gastropub menu: You’re chasing a trend that’s well past its peak, which makes you a cliché. But if the local dining scene’s a decade late, the fashion scene’s at least that tardy, so I wasn’t concerned. I wore the jacket with a plain, dark grey t-shirt and medium stonewash Levi’s held up by a white Louis belt.

In another obligatory nod to local custom, I brought out a pair of white Air Force 1s with “cosmic clay” tips, eyestays, tongues and backtabs. I despise them, but they garner compliments in downtown Knoxville, “cosmic clay” being a very close cousin to “Tennessee orange.” Last but certainly not least in the tacky department, I brought along my bright-orange Goyard Saint-Sulpice card wallet. That’s a “just for Knoxville” accessory, and like the “cosmic clay” Forces, it’s a real crowd pleaser on Rocky Top.

My first stop was Nama for a sushi appetizer. I had a caterpillar roll, which was predictably unremarkable. Of course, no one who’s serious about sushi orders a caterpillar roll. Let me go a bit further: No one who’s serious about sushi would ever eat it at a place that serves caterpillar rolls. But that’s precisely why I ordered it. If you’re seeking transcendence through sushi, you go to Tokyo, not Tennessee. If you’re in Tennessee, you really shouldn’t be eating sushi at all, but if you’re hell-bent on it, do yourself a favor: Order something that couldn’t make you sick even if it tried.

Next was Emilia and here I should be honest: I’m not impartial. I was smitten from my first meal there three or four years ago. It’s cozy without being cramped, intimate without being schmaltzy and upscale without trying. The occasional menu tweak makes Emilia’s “local ingredients” pitch believable (eggplant parmesan’s seasonal), and the food’s pricey enough to flatter my vanity but not so pricey as to flatter itself. Familiar faces among patrons and, just as importantly, among the small waitstaff, are comforting on multiple levels.

I grabbed a seat at the bar and asked after an espresso machine that’s been in a bad way for too long. It was still on the fritz so I settled for coffee. You can’t go to Emilia without ordering the focaccia, which they get from a local baker and serve warm with ricotta. I called for some of that straight away. Roasted beets with pistachio butter sounded mandatory, so I ordered those too.

The menu promised at least a hint of white balsamic vinegar in the beets. That promise proved empty and the dish suffered immeasurably for it. Being a beet lover and an avowed pistachio fan I would’ve ordered it anyway, but if you’re going to pair the most quintessentially earthy ingredient known to man with “butterized” pistachios, you better add some acidity lest you should end up with something that’s unpalatably — inedibly — rich.

Wanting to avoid what might’ve been my first subpar experience in at least two dozen visits to Emilia, I went the safe route for the main: Mafalde with zucchini alla Nerano, mushrooms and toasted pine nuts. I’ve had that dish at Emilia on several occasions. It’s reliably good, with the important caveat that a persnickety culinarian probably wouldn’t recognize it as authentic.

Zucchini alla Nerano’s a “simple” dish about like nigiri’s “just” sliced fish on a ball of rice, which is to say there’s zucchini alla Nerano and then there’s zucchini alla Nerano. Geographical context matters quite a lot. If you’re in Sorrento, the dish should be little short of sublime. To expect that from zucchini alla Nerano anywhere other than the Amalfi Coast is a ridiculous ask, particularly considering the distinct possibility that what makes zucchini alla Nerano served in Campania sublime isn’t the dish at all (the ingredients aren’t exactly exotic), but rather the surroundings.

I left Emilia full, but not so full I couldn’t make room for a cup of ice cream. The line at Cruze Farm was out the door and around the corner, as it always is in the evenings. I took my place and waited. When it was my turn I ordered sugar cookie-flavored soft serve, paid from the orange card wallet (“I love that! So cute!” said one of the gingham-clad cashiers) and took a seat in the crowded parlor, not bothering to hide a childlike excitement I’d otherwise suppress lest someone should mistake me for affable.

The next night was the main event for my trip: A full-dress historical reenactment of yesteryear’s Goodfellas pastiche. A cosplay of the cosplay. Some of the characters were missing, lost over the years to jail or worse, but the leads were all present, accounted for and, by the grace of a god who’s inclined to excessive forgiveness in my case, thriving.

I chose J.C. Holdway for the occasion. The passion project of James Beard Award winner and Blackberry Farm veteran Joseph Lenn, J.C. Holdway landed on The New York Times‘s 50 Best Restaurants in America list for 2025 and on USA TODAY’s Best Restaurants in the Country list for 2026. For eight or so months in 2023 I was a regular at the bar, where I garnered a reputation for drinking a lot of coffee and leaving large tips.

I hesitate to rank J.C. Holdway among the 50 best restaurants in all of America, a country with 39 two-Michelin-star kitchens. But I’m quite comfortable pronouncing it the best restaurant in Knoxville. That’s as objective an assessment as it’s possible to make about an inherently subjective experience like eating. Knoxville simply doesn’t have another kitchen run by a chef of Lenn’s caliber.

When the Times says Lenn’s “a constant presence in J.C. Holdway’s open kitchen,” they aren’t exaggerating. He’s there almost every night. I chatted with him on more occasions than I can remember in 2023. His then-fiancée taught finance at the university. I imagine we’re the only two people to ever discuss CDS spreads at a restaurant in downtown Knoxville.

For my retinue reunion dinner, I jettisoned any pretense to humility in favor of a navy Versace shirt adorned with the iconic Medusa head logo printed in different shades of blue. I paired it with brown jeans, a brown Louis LV initiales belt and a garish pair of Air Force 1s paneled in different shades of denim that matched the shirt. The gum soles matched the jeans and the belt.

I brought gifts for the top members of my old entourage: Gucci accessories monogrammed with “XX” to celebrate 20 years since the establishment of a pact that often blurred the line between Cosa Nostra cabaret and racketeering.

Although I was too swept up in the moment to accord the food the attention it deserved, I can say Lenn delivered a meal worthy of the occasion and of the historical occasions it was meant to invoke.

Cheddar pimento cheese sharp enough to squeeze your cheeks (in a good way) was a textural delight and an heirloom tomato “risotto” (the “risotto” was actually Carolina gold rice) proved savory enough to punch through a liberal application of lush parmesan cream drizzled with a grape reduction.

Lenn’s signature dish — confit broth with gnocchi and wild mushrooms that thickens into a classic chicken and dumplings when you cut into a slow-cooked farm egg placed in the middle — was the definition of “elevated comfort food.”  

We had campanelle with a corn basil pistou. And the same pork belly biscuits lauded by the Times. And Lenn’s Weisenberger Mill cornbread with a sorghum butter so good it could pass for a standalone dessert. 

The mains — black angus ribeye with soubise, roasted chicken and a whole grilled trout “suavely deboned before our eyes” at the table, just as described by the Times — were all executed to something indistinguishable from perfection, with the caveat that none of the preparations were inherently demanding.

During dessert, a quintessentially suburban woman seated with her husband at the table nearest ours photobombed one of the group portraits I compelled the waitstaff to capture. Taking her cues from the assemblage of couture gift bags and typecasting from the eclectic mix of characters I’d assembled, she squinched her face into a mock, pursed-lip frown and flashed a sideways peace sign as the shutter snapped. I had well and truly succeeded in creating the optics I set out to conjure. 

Sky-high on glorious nostalgia, I swaggered back to the hotel confident that the past can be recaptured after all. That you can, in fact, “go home again.” 

The next day, around noon, I got a text from my childhood best friend informing me that a mutual acquaintance of ours in Knoxville died early that morning. “Christ, from what?” I asked, already knowing the answer. “Heart attack, apparently. He tried to go cold turkey.” 

I wasn’t responsible, of course. 15 years is a very long time. Still, I couldn’t shake the suspicion that, consciously or not, my old friend was invoking the butterfly effect while alluding to some manner of far-removed, moral culpability. 

I sat with that for a minute. A mother, who I knew well, was shattered that day. A sister, who I also knew well, likewise broken apart. Suffering. Hopelessness. Pain.

I swiped the text window up and away on my iPhone, opened the photo album and scrolled back through the previous evening’s “family portraits.” Ease. Hope. Joy.

Emilia

J.C. Holdway